Sodium borohydride → HCID 67019977, compound

Participants

Reaction Steps

2-Ethyl-4-[(1R)-2,2,3-trimethylcyclopentyl]but-2-enal (3a; 8.5 g, 41 mmol) was added dropwise within 10 min. to a stirred suspension of sodium borohydride (1.9 g, 50 mmol) in ethanol (100 ml) at 5-10° C. After additional 2 h stirring at room temperature, the reaction mixture was poured into an ice-cold 0.1 N HCl solution and extracted with MTBE (200 ml). The extract was washed with ice-cold brine (2×100 ml), dried (MgSO4), concentrated in vacuo and the residue was distilled under reduced pressure to give 2-ethyl-4-[(1R)-2,2,3-trimethylcyclopentyl]but-2-en-1-ol (4a) which was further purified by flash chromatography (MTBE/hexane 1:5; 5.8 g, 68% yield, colourless liquid; GC/MS: 2 isomeric pairs of enantiomers 0.5+88.5%).

Provenance & Evidence