Tetrahydrofuran → Phenyl(8-thiabicyclo[3.2.1]oct-3-yl)methanone
Reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9]12[S:16][CH:13]([CH2:14][CH2:15]1)[CH2:12][CH:11]([C:17]#N)[CH2:10]2.C1C[O:22]CC1>>[C:1]1([C:17]([CH:11]2[CH2:12][CH:13]3[S:16][CH:9]([CH2:15][CH2:14]3)[CH2:10]2)=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
4
Procedure
A 3M etheral solution of phenyl magnesium bromide (6.72 ml, 20.16 mmol) was added at 0° C. to a solution of the above nitrile (1.03 g, 6.72 mmol) in dry THF (10 ml). After 30 minutes, the ice bath was removed and the reaction continued at room temperature for 16 hours. The reaction was carefully quenched by addition of a saturated aqueous NH4Cl solution. After addition of ether, organic layer was separated, washed with brine, dried over MgSO4 and concentrated. The residual oil was chromatographied on silica gel (hexane/AcOEt 94/6) to give the phenyl(8-thiabicyclo[3.2.1]oct-3-yl)methanone 22 as a colorless oil (586 mg, 38%).