Benzaldehyde → 1-Phenyl-1-propanol

Participants

Reaction Steps

(+)-Me-IAN amine (19.0 mg, 66.8 μmol) was dissolved in toluene (0.85 mL) in a 10 mL flask. Et2Zn (1.22 mL, 1.1 M in toluene, 1.34 mmol) was added in one portion via syringe. Immediately, a clear red-orange solution formed. After stirring for 30 min., benzaldehyde (0.068 mL, 0.669 mmol) was added. This addition immediately lightened the solution to a pale orange-yellow. After 19 h, the solution returned to its red-orange color. Water was added and the mixture was extracted three times with CH2Cl2. The combined organic phases were dried over MgSO4, filtered, and concentrated iii vacuo. Purification of the crude product via flash column chromatography on silica gel gave 1-hydroxy-1-phenylpropane as a light yellow liquid (28.6 mg, 31.4%). HPLC analysis of the product (OD column, 1.0 mL/min, 2% iPrOH in hexanes) gave 85.2% ee (retention time of major peak=13.7 min, retention time of minor peak=16.3 min) and a decrease in the ee of (+)-Me-IAN amine (from 99% to 93.2% ee).

Provenance & Evidence