Ammonia → HCID 13075708, compound

Participants

Reaction Steps

To a solution of 1.2 g of lithium in 80 ml of liquid ammonia (distilled over Na) was added 443 mg of the epoxide (4) in THF (70 ml) dropwise during 1 hr under dry ice-acetone bath cooling and then the reaction mixture was stirred for 1 hr at reflux. The reaction mixture was recooled by dry ice-acetone bath and to this was added solid NH4Cl (12 g) in small portions during 1 hr, then refluxed for 3 hr. After bubbling argon gas to remove NH3, water was added to the reaction mixture and this was extracted with AcOEt. The extract was submitted to silica gel column chromatography. The fraction eluted with n-hexane and AcOEt (1:2) afforded 274 mg (65%) of the triol (5), mp 201°-202° C. (from CHCl3), MS Calcd. for C27H40F6O3 : 526.2879. Found: 526.2878. NMR(CDCl3) and acetone-D6 δ0.69(s, 18-H3), 0.93(d, J=6 Hz, 21-H3), 1.03(s, 19-H3), 3.83(1H, m, 1-H), 4.00(1H, m, 3-H), 5.53(1H, m, 6-H).

Provenance & Evidence