Butanal → HCID 86657764, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-2-methyl-propane-2-sulfinamide (6.7 g, 55 mmol) in dichloromethane (125 mL) is added butyraldehyde (4.0 g, 55 mmol) followed by titanium isopropoxide (32 g, 110 mmol). The reaction is then heated at reflux (bath temperature=60° C.) for 4 hours. The resultant mixture is cooled to room temperature and poured into a stirred mixture of diatomaceous earth (10 g) and water (100 mL). The slurry is stirred for 10 min and then filtered. The organic layer from the filtrate is concentrated in vacuo to afford a crude yellow oil which is purified by flash chromatography on silica gel (eluted with 5 to 30% dioxane/hexanes) to afford (S)-2-methyl-propane-2-sulfinic acid butylideneamide as a colorless oil (7.4 g, 77%).

Provenance & Evidence