Benzaldehyde → 1-Phenyl-2-(pyridin-2-yl)propan-1-ol

HRID 907486Notes

Reaction equation

C([Li])CCC.[CH2:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:7].[CH:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[C:15]1([CH:14]([OH:21])[CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH3:7])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: -60 °C

Procedure

n-Butyllithium (2.5 M, 15.0 mL, 36.0 mmol) is added drop wise to a solution of 2-ethylpyridine (4.1 mL, 36.0 mmol) in THF (56 mL) at −40° C. The resulting dark red solution is kept at −30° C. to −20° C. for 1 hour and then cooled to −60° C. A solution of benzaldehyde (3.7 mL, 36.0 mmol) in THF (10 mL) is added drop wise. The reaction mixture is allowed to warm up to 0° C. for 1 hour and then quenched with aqueous NH4Cl solution. The mixture is separated and the aqueous phase is extracted with ethyl acetate (2×50 mL). The extracts are combined, dried, concentrated and purified by column chromatography (hexane/ethyl acetate 10:1 to 1:1) to give 2 (7.0 g, 91%) as a yellow oil. This mixture contained two diastereoisomers (3:1). 1H NMR (300 MHz, CDCl3) for the major isomer: δ 1.14 (d, J=7.2 Hz, 3H), 2.98 (q, J=6.9 Hz, 1H), 4.70-4.75 (m, 1H), 5.13-5.16 (m, 1H), 6.80-7.39 (m, 8H), 8.34 (d, J=4.8 Hz, 1H).

Workup

temperatureto warm up to 0° C. for 1 hour
customquenched with aqueous NH4Cl solution
customThe mixture is separated
extractionthe aqueous phase is extracted with ethyl acetate (2×50 mL)
customdried
concentrationconcentrated
custompurified by column chromatography (hexane/ethyl acetate 10:1 to 1:1)

Sources & evidence

ORD record: ord-1a034842d58143538e55969f51403f66
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013165B2

Reaction notes

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