Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1.[Li]CCCC.[CH:14]12[O:20][CH:19]1[CH2:18][CH2:17][CH2:16][CH2:15]2.B(F)(F)F.CCOCC.[Cl-].[NH4+]>C1COCC1>[C:4]1([CH3:8])[CH:5]=[CH:6][CH:7]=[CH:2][C:3]=1[CH:18]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:19]1[OH:20]
To a solution of 1-bromo-3-methyl-benzene in THF at −78° C., was added dropwise a solution of nBuLi (1.6M in THF, 12.4 ml) and the reaction mixture was stirred at −78° C. for 30 minutes. After such time, 7-oxa-bicyclo[4.1.0]heptane (3.4 g) was added slowly to the reaction mixture followed by the addition of boron trifluoride etherate (2.5 ml). The reaction mixture was stirred at −78° C. for another 2 hours before allowing it to warm up to room temperature. The solution was then treated with solution of ammonium chloride (25 ml), the phases were separated and then extracted twice with ethyl acetate. The combined organic extracts were then washed with water, dried over sodium sulfate and concentrated in vacuo. The residue was then purified by column chromatography to give 2.9 g of (cis/trans) 2-o-tolyl-cyclohexanol MS(EI) 190.1 (M+).
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