[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH:10]([N:13]([CH2:16][CH3:17])[CH:14]=O)[CH2:9][CH2:8][C:7]=2[CH:18]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[F:1][C:2]([F:19])([F:20])[C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH:10]([N:13]([CH2:16][CH3:17])[CH3:14])[CH2:9][CH2:8][C:7]=2[CH:18]=1A solution of 285.3 g of 2-trifluoromethyl-7-(N-ethyl-N-formylamino)-6,7,8,9-tetrahydro-[5H]-benzocycloheptene in 3700 ml of anhydrous ether is introduced over a period of one hour into a suspension of 56 g of lithium aluminum hydride in 4700 ml of anydrous ether while stirring (a gentle reflux is observed). The whole is then heated at the boil for 5 hours. After cooling, the reaction mixture is hydrolysed in succession with 56 ml of water, 56 ml of a solution of 4N sodium hydroxide and 170 ml of water. After filtration and washing with ether, the organic layer is concentrated in vacuo and the residue is distilled off. 150 g of 2-trifluoromethyl-7-(N-ethyl-N-methylamino)-6,7,8,9-tetrahydro-[5H]-benzocycloheptene are obtained, b.p./10 mm =135°-140° C.
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