Methanol → 1-Phenylethanol

Participants

Reaction Steps

The acetate R-2a (164 mg; 1.0 mmol) was deacetylated by overnight treatment with potassium carbonate (276 mg; 2.0 mmol; 2 equiv.) in methanol (3 mL). The product R-1a (89 mg; 73%) was isolated by dilution with water (25 mL), extraction with ether (2×10 mL), drying of the extracts (MgSO4), and concentration. All achiral properties of 1a are as reported above. 1H nmr analysis of the MTPA ester using an analogous procedure to that of Dale et al., J. Org. Chem., 1969, 34, 2543, indicated 90% ee for R-1a. [α]D20 +40.3° (c. 1.06, CH3OH).

Provenance & Evidence