1-Propanol → HCID 21678418, compound

Participants

Reaction Steps

preparation of 3-(tert-Butyldimethylsilyloxy)-2-benzylpropanal (4). Dimethylsulfoxide (3 ml) was added dropwise to a solution of 1.10 g (8.67 mmol) of oxalyl chloride in 30 ml of methylene chloride at -78° C. This solution was stirred and a solution of 2.08 g (7.42 mmol) of the propanol it in 10 ml of dimethylsulfoxide was added. The resulting mixture was stirred for 20 minutes and then 7.6 ml (54.4 mmol) of triethylamine was added. After being stirred for an additional 20 minutes, the mixture was poured into 100 ml of water. The layers were separated. The aqueous phase was extracted with methylene chloride. The combined organic phases were dried and concentrated. The residue was purified on a silica gel column with 3:2 ether/hexane to give 1.84 g (90%) of 3 as a colorless liquid; 1H NMR (CDCl3) δ0.12 (s, 6H), 0.91 (s, 9H), 2.60 (m, 1H), 2.71 (m, 1H), 2.98 (m, 2H), 3.63 (m, 1H), 3.81 (m, 1H), 7.09 (m, 5H); IR (neat); 2931, 2860, 1730, 1471, 1255, 1100, 846 cm-1.

Provenance & Evidence