[4-(Chloromethyl)phenyl]phenylmethanone

White Solid

General procedure: To a stirred solution of the O7-demethyl glaziovianin A (10) (10.0 mg, 26.8 mumol) in MeCN (2.0mL) were added K2CO3 (11.4 mg, 82.4 mumol) and 4-chlorobenzyl bromide (16.3 mg, 79.5 mumol) at roomtemperature. After being stirred at room temperature for 18 h, the reaction mixture was diluted withsaturated aqueous NaHCO3 (2.0 mL) and extracted with CHCl3 (10 mL × 3). The combined extracts werewashed with brine, dried (Na2SO4), filtered, and concentrated. The crude product was purified by columnchromatography on silica gel (700 mg, nhexane-EtOAc = 3 : 1 ' CHCl3) to give O7-4-chlorobenzylgatastatin (11) (13.3 mg, quant);Diaryl ketone 3q (115 mg, 0.5 mmol) and sodium cyanide (49 mg, 1.0 mmol) were dissolved in 1, 4-dioxane/H2O=7:3 (15 mL). The mixture was heated under reflux for 2 h, during which the organic product appeared as a separate layer. The cooled reaction mixture was extracted with EtOAc (2*10 mL). The combined organics were concentrated with a rotary evaporator to give yellow solid. After purification by column chromatography on silica gel (hexane/ethyl acetate=2:1, Rf=0.46) 4 (57 mg, 1.3 mmol, 51%) was obtained as pale yellow solid. 1H NMR (300 MHz, CDCl3): delta 3.84 (s, 2H), 7.44-7.51 (m, 4H), 7.57-7.63 (m, 1H), 7.76-7.82 (m, 4H).i Part A: p-Chloromethylbenzophenone. A solution of 100 g (0.51 mol) of p-methylbenzophenone (Aldrich), 130 ml of carbon tetrachloride, 98 g of sulfuryl chloride, and 55 mg of dibenzoyl peroxide was heated at reflux under nitrogen. At 2-h intervals, three additional 50 to 70-mg portions of dibenzoyl peroxide were added. After 18 h a final 50-mg portion of dibenzoyl peroxide was added. After 1 h, unreacted sulfuryl chloride was removed by co-distillation with carbon tetrachloride (b.p. 69). To the residue containing carbon tetrachloride, was added 5 g of potassium carbonate and 5 g of Woelm basic alumina. The mixture was refluxed for 15 min with stirring, and then filtered hot to give 57 g of crystals after cooling. Recrystallization from ethanol yielded 44.7 g (38%) of colorless crystals (m.p. 95-96); m.p. 98 NMR delta4.60 in CDCl3.Part B: N-Acetyl-alpha-Cyano-p-Benzoyl-DL-Phenylalanine Ethyl Ester. A stirred mixture of 41.9 g (181 mmol) of

Molecular Weight:230.69
XLogP3:3.7
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:230.0498427
Monoisotopic Mass:230.0498427
Topological Polar Surface Area:17.1
Heavy Atom Count:16
Complexity:225
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes