Triethylsilane → 3-(4-Bromo-3,5-dimethylphenyl)-2,5-dihydrofuran

Reaction equation

C([SiH](CC)CC)C.[Br:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[CH:20]=[CH:19][O:18][CH:17]=2)=[CH:11][C:10]=1[CH3:21].C([O-])(O)=O.[Na+]>FC(F)(F)C(O)=O>[Br:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[CH2:17][O:18][CH2:19][CH:20]=2)=[CH:11][C:10]=1[CH3:21]

Participants

Procedure

Triethylsilane (3.67 mL) is added dropwise to a solution of 3-(4-bromo-3,5-dimethylphenyl)furan (580 mg) in trifluoroacetic acid and the resulting mixture is stirred at room temperature for 3 h. Saturated aqueous NaHCO3 solution is added and the aqueous phase is separated and extracted with ethyl acetate. The combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 95:5) to give the title compound. LC (method 9): tR=1.16 min; Mass spectrum (ESI+): m/z=251, 253 [M+H]+.