C([Li])CCC.Br[C:7]1[CH:11]=[CH:10][O:9][CH:8]=1.[CH3:12][C:13]1[C:17]2[CH2:18][CH2:19][CH2:20][C:21](=[O:22])[C:16]=2[O:15][N:14]=1.[Cl-].[NH4+]>CCCCCC.CCOCC>[O:9]1[CH:10]=[CH:11][C:7]([C:21]2([OH:22])[C:16]3[O:15][N:14]=[C:13]([CH3:12])[C:17]=3[CH2:18][CH2:19][CH2:20]2)=[CH:8]1To a solution of 4 ml (0.04 mol) of 10M n-butyllithium in hexane cooled to -78° C. was added 3.59 ml (0.04 mol) of 3-bromofuran in 100 ml of ether and the mixture was stirred for 10 min. To the above cooled solution was added 5.49 g (0.036 mol) 4,5,6,7-tetrahydro-3-methyl-benzisoxazol-7-one and the mixture was allowed to warm to room temperature, and then stirred for 1 h. To the mixture was added saturated ammonium chloride solution and the resulting mixture was extracted with ethyl acetate (3×100 ml), and the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to afford 7.6 g (96%) of 7-(3-furyl)-3-methyl-4,5,6,7-tetrahydrobenzisoxazol-7-ol, as a brown oil.
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