2,6-Dichlorobenzeneethanol

white to slightly yellow crystalline powder,

(vii) 2, 6-Dichlorophenethyl alcohol: a suspension of lithium aluminum hydride (13.75 g, 365.75 mmol) in anhydrous diethyl ether (500 mL) was added via a powder addition funnel 2, 6-dichlorophenylacetic acid (50 g, 243.75 mmol). The resulting reaction mixture was refluxed for 16 hours and then quenched by slow addition of a sodium sulfate saturated aqueous solution (25 mL). The resulting slurry was stirred for 3 hours and then filtered, the insoluble was carefully washed with diethyl ether (2 x 100 mL). The combined ether filtrates were dried over sodium sulfate and the solvent was evaporated in vacuo to yield 38.6 g (85percent yield) of the title compound.To a solution of 2-(2, 6-dichlorophenyl)ethan- 1-ol (20 g, 104.68 mmol, 1.00 equiv) in pyridine (500 mL) was added sodium hydride (5.2 g, 216.67 mmol, 1.25 equiv). The resulting solution was stirred at 0 C for 1 h. Then CuC1 (600 mg, 6.12 mmol, 0.05 equiv) was added. The resulting solution was stirred overnight at 115C. The resulting mixture was concentrated under vacuum. The reaction was then diluted with 500 mL of H20. The pH value of the solution was adjusted to 4 with HC1 (3 M). The solids were filtered out. The resulting solution was extracted with petroleum ether. And the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The cmde product was purified by 5i02 chromatography, eluted with petroleum ether to afford 16 g (99%) of 4-chloro-2, 3-dihydro-1-benzofuran as colorless oil.Under nitrogen protection, 250 g2, 6-dichlorophenylethyl alcohol, 6. 46 g of CuCl and 5.75 g of ethyl acetate with 7. 5 LTetrahydrofuran. Add 104.43 g NaH in batches while maintaining the temperature below 70 C. The resulting mixture was stirred at 70 C for 18 hours. The mass fraction of the starting material in the reaction system was controlled by gas chromatography <10%. The mixture was cooled to 5 to 10 C. Add 165 g of acetic acid while maintaining the temperature below 30 C. Add 1 L of water. The solvent is removed as far as possible at temperatures below 40 C. 2 L of heptane was added, and the resulting mixture was stirred for 10 minutes. After standing, the organic layer was separated and dried over MgSO4. The dried mixture was filtered and the filter cake was washed with 100 mL of heptane. The filtrates were combined and 80 g of silica gel was added to the combined filtrate. After sufficiently stirring, the filter was filtered and the filter cake was washed with 100 mL of heptane, and the filtrate was combined. Remove the solvent at 40 to 45 C. To obtain 220 g of an oil, 4-chloro-2, 3-dihydrobenzofuran crude extract in a yield of 109% and a purity of 89%.Synthesis Example 20: Compound No.125 (2S, 3R, 4R, 5S, 6R)-2-(4-chloro-5-(chroman-6-ylmethyl)-2, 3-dihydrobenzofuran-7-yl)-5-fluoro-6-(hydroxymethyl)-tetrahydro-2H-pyran-3, 4-diol To a mixture of Under the protection of argon, Weigh compound 5-2 (0.5 g, 2.62 mmol) in anhydrous toluene (8 mL), Add sodium hydride (0.131 g, 3.28 mmol), After heating to 40 C and stirring for 15 minutes, Cool the reaction to room temperature, Cuprous chloride (13 mg, 0.131 mmol) was added, Toluene (2 mL) and ethyl acetate (0.013 mL) were subsequently added, Heated to 120 C and refluxed for 24h, After the reaction is completed, the reaction solution is cooled to room temperature. Slowly add ice water to quench the sodium hydride, filter to remove insoluble matter, The filtrate was diluted with water and transferred to a separating funnel. Extract with methyl tert-butyl ether (10 mL x 3), combine the organic phases, The organic phase was washed with saturated brine (5 mL x 3), dried over anhydrous sodium sulfate, The solvent was distilled off under reduced pressure, The residue was purified by column chromatography (eluent: petroleum ether / ethyl acetate = 50: 1), Compound 5-3 (light yellow liquid, 0.25 g) was obtained.

Molecular Weight:191.05
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:189.9952203
Monoisotopic Mass:189.9952203
Topological Polar Surface Area:20.2
Heavy Atom Count:11
Complexity:109
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes