1-Butanol → HCID 9881978, compound

Participants

Reaction Conditions

Reaction Steps

First, 106 mg (purity of 84%, 0.72 mmol) of cyclohexylidene acetaldehyde, 120 mg (0.72 mmol) of benzenesulfonyl cyanide, 17 mg (0.072 mmol) of tributyl borate, 11 mg (0.14 mmol) of 1-butanol, and molecular sieves 4A (310 mg) as dehydrator were introduced to a flask (5 ml volume). Toluene (1.5 ml) was added as the solvent, and the mixture was heated for 14 hours at an internal temperature of 110° C. After this solution was cooled to room temperature, the molecular sieves was filtered off and the low-boiling components, such as solvent, etc., were removed under reduced pressure to give the desired, crude product. The crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=⅓) to give 31 mg of 1-benzenesulfonyl-5,6,7,8-tetrahydroisoquinoline with the following properties as yellow crystals (yield of 16% based on benzenesulfonyl cyanide).

Provenance & Evidence