Acetaldehyde → 4-Phenyl-3-butyn-2-ol

Participants

Reaction Steps

Phenylacetylene (5.5 mL; 50 mmol) was dissolved in THF (40 mL) and cooled to -78°. A 1.35M solution of n-butyllithium in hexane (37 mL; 50 mmol; 1.0 equiv.) was added dropwise and the resulting mixture was stirred at -78° for 1 h. Acetaldehyde (2.8 mL; 50 mmol; 1.0 equiv.) was added and the reaction mixture was allowed to warm overnight to room temperature. The mixture was diluted with ether (50 mL) and washed with water (3×25 mL). The organic solution was dried (MgSO4) and concentrated, and the crude product was distilled in vacuo, affording 3.4 g (47%) of 1f, bp 94° C./approximately 2 mm Hg. 1H nmr (300 MHz, CDCl3): 7.444-7.261 (5H, m); 4.762 (1H, q, J=5 96 Hz); 1.972 (1H, s); 1.557 (3H, d, J=6.58 Hz). IR (neat film, cm-1): 3400 (s); 1600 (w). FDMS (m/e): 146 (M+).

Provenance & Evidence