Hydrochloric Acid → HCID 67275537, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-(1-azido-2,2-dimethylpropyl)-4-(propylthio)benzene (282 mg, 1.07 mmol) in THF (8 ml) were added triphenylphosphine (842 mg, 3.21 mmol) and water (2 ml). The mixture was heated at 50° C. for 18 hours then allowed to cool to room temperature. Methanol (10 ml) was added and the mixture was passed through an SCX cartridge, which had been pre-treated with HCl in MeOH, eluting first with several column lengths of methanol to remove the triphenylphosphine oxide, then with 2M solution of ammonia in methanol to elute the product. The appropriate fractions were evaporated to give the title product as a pale yellow oil (231 mg). 1H NMR 3 (CDCl3) 7.27-7.19 (4H, m), 3.67 (1H, s), 2.89 (2H, t, J=7.3 Hz), 1.72-1.62 (2H, m), 1.02 (3H, t, J=7.3 Hz), 0.89 (9H, s).

Provenance & Evidence