5-Acetyl-1,3-benzodioxole

BEIGE CRYSTALLINE POWDER

3,4-Methylenedioxyacetophenone is a member of benzodioxoles.

General procedure: Method B: to a solution of compound 4a (1.65 g, 9.94 mmol) inanhydrous CH2Cl2 (100 mL) stirred at 0 C under argon was addedDess-Martin reagent (5.06 g, 11.93 mmol). The mixture was allowedto warm to room temperature after 10 min and stirred for 16 h. Thereaction was quenched with a saturated sodium bicarbonate solution and salts were filtered off. The filtrate was extracted withCH2Cl2. The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure. Purification bysilica column chromatography using CH2Cl2 as eluent gave thedesired ketone 5a (1.42 g, 87percent) as a pale yellow solid.General procedure: In an oven dried Schlenk tube, were added alcohol 1 (69.0–199.5 mg, 0.5 mmol), CuI (10 molpercent)and 1, 10-Phenanthroline (20 molpercent) and K3PO4 (2 mmol) followed by the addition of dioxane (2mL) at room temperature under open air atmosphere. The stirred reaction mixture was heated inan oil bath at 80 C for 7–48 h. Progress of the reaction was monitored by TLC till the reaction iscompleted. Then, the reaction mixture was cooled to room temperature, quenched with aqueousNH4Cl solution and then extracted with CH2Cl2 (3 10 mL). The organic layer was washed withsaturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent under reducedpressure and purification of the crude material by silica gel column chromatography (petroleumether/ethyl acetate) furnished the aldehyde/ketone 2 (61–97percent).General procedure: Into a Schlenk flask were introduced 20 mL of nitromethane, 2 mmol of 1, 3-dimethoxybenzene, 10 mol percent of catalyst and4 mmol of acetyl chloride, with 0.5 mmol of dodecane for GC monitoring. The solutions were heated at reflux. The reactionswere followed by gas chromatography, by analysis of aliquots.The products were obtained after extraction by diethyl ether andpurification by column chromatography. All products are knowncompounds.In a 1 L three-opening in the bottle, by adding dichloromethane 500 ml, aluminum chloride/polystyrene (66.5 g, loading 10 wt percent), stirring slowly under the condition into the acetyl chloride (42.9 g, 5.5 µM), the completion of the dropping, then gradually dripped into the pepper link (61.0 g, 0.5 µM, dissolved in 100 ml dichloromethane); after dropping, slow heating to 45 °C stirring reaction, until the pepper ring reaction finishes, cooling, filtering to obtain aluminum chloride/polystyrene catalyst; the reaction liquid layered extraction, the combined organic layer, evaporating the solvent under reduced pressure, drying to obtain products 77.2 g, yield 94percent.General procedure: An oven-dried vial was charged with anisole 1a (0.75 mmol, 1.0 equiv), acetic anhydride 2a (1.5 mmol, 2.0 equiv) and TFA (0.8 mL). The reaction mixture was stirred at room temperature and monitored by TLC or GC-MS. The reaction typically took 1.5 h to complete. Upon completion, aqueous sodium hydrogen carbonate was added and the aqueous phase was extracted with ethyl acetate (3 x 20 mL). The combined organic layers were dried over NaIn a 1 L three-opening in the bottle, adding trifluoromethylbenzene 500 ml, zinc chloride/three-alumina (272.6 g, loading 10 wt percent), stirring slowly under the condition into the acetic anhydride (56.1 g, 0 . 55 µM), the completion of the dropping, then gradually dripped into the pepper link (61.0 g, 0.5 µM, dissolved in 100 ml trifluoromethylbenzene); after dropping, slow heating to 120 °C stirring reaction, until the pepper ring reaction finishes, cooling, filtering to obtain the zinc chloride/three-alumina catalyst; the reaction liquid layered extraction, the combined organic layer, evaporating the solvent under reduced pressure, drying to obtain products 73.9 g, yield 90percent.In a 1 L three-opening in the bottle, to join the nitrobenzene 500 ml, aluminum chloride/silicon dioxide (166.3 g, loading 10 wt percent), stirring slowly into the acetic acid under the condition (33.0 g, 0 . 55 µM), the completion of the dropping, then gradually dripped into the pepper link (61.0 g, 0.5 µM, dissolved in 100 ml of nitrobenzene); after dropping, slow heating to 80 °C stirring reaction, until the pepper ring reaction finishes, cooling, filtering to obtain aluminum chloride/silicon dioxide catalyst; the reaction liquid layered extraction, the combined organic layer, evaporating the solvent under reduced pressure, drying to obtain products 78.8 g, yield 96percent.N-methoxy-N-methylbenzo[d][1, 3]dioxole-5-carboxamide. To a solution of acid 290 40 (1.0g, 6.01mmol) in dry 196 DCM (20mL), EDCI (1382mg, 7.21mmol), 291 HOBt (974mg, 7.21mmol) and 76 N, N-DIPEA (2mL, 12.01mmol) were added at 0°C. The reaction mixture was stirred at 0°C for 30min, then 292 N, O-dimethylhydroxylamine hydrochloride (703mg, 7.21mmol) and N, N-DIPEA (1.00mL, 6.01mmol) were added. The reaction mixture was stirred at 25°C for 12h, then quenched with saturated aqueous NaHCO

Used as a pharmaceutical intermediate, used to synthesize drugs to prevent and treat high cholesterol and coronary atherosclerosis, and also to synthesize a new class of sulfonamide antibacterial and anti-inflammatory drugs

Molecular Weight:164.16
XLogP3:0.6
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:164.047344113
Monoisotopic Mass:164.047344113
Topological Polar Surface Area:35.5
Heavy Atom Count:12
Complexity:190
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes