(4-chlorophenyl)(pyridin-3-yl)Methanol synthesis
- Product Name:(4-chlorophenyl)(pyridin-3-yl)Methanol
- CAS Number:68885-32-5
- Molecular formula:C12H10ClNO
- Molecular Weight:219.6669
14548-44-8
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68885-32-5
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Yield:68885-32-5 97%
Reaction Conditions:
with sodium tetrahydroborate in methanol at 20; for 48 h;Inert atmosphere;
Steps:
Preparation of diarylmethanol intermediates (6) from benzophenones.
(4-Chlorophenyl)(pyridin-3-yl)methanol (9). To a solution of (4-chlorophenyl)(pyridin-3-yl)methanone (3g, 14mmol) in methanol (20mL) was slowly added sodium borohydride (0.72g, 20mmol). The mixture was stirred at room temperature under nitrogen for 48 h, then concentrated, diluted with water (40mL) and extracted with chloroform (40mL). The organic layer was dried, filtered and the filtrate concentrated to afford 9 as a white solid (2.98g, 97%). 1H NMR (300 MHz, CHLOROFORM-d) d 8.54 (d, J = 2.0 Hz, 1H), 8.46 (dd, J = 4.8, 1.4 Hz, 1H), 7.60 - 7.76 (m, 1H), 7.21 - 7.36 (m, 5H), 5.85 (d, J = 2.3 Hz, 1H), 3.27 (br. s., 1H).
References:
Keenan, Martine;Alexander, Paul W.;Diao, Hugo;Best, Wayne M.;Khong, Andrea;Kerfoot, Maria;Thompson, R. C. Andrew;White, Karen L.;Shackleford, David M.;Ryan, Eileen;Gregg, Alison D.;Charman, Susan A.;Von Geldern, Thomas W.;Scandale, Ivan;Chatelain, Eric [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 7,p. 1756 - 1763] Location in patent:supporting information
