[CH:1]([CH:3]1[CH2:5][C:4]1([C:11](OCC)=[O:12])[C:6](OCC)=[O:7])=[CH2:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1.C1CCCCC1.C(OCC)(=O)C>[OH:7][CH2:6][C:4]1([CH2:11][OH:12])[CH2:5][CH:3]1[CH:1]=[CH2:2]A solution of 23 g (0.108 mole) of diethyl 2-vinylcyclopropane-1,1-dicarboxylate in 90 ml of dry THF (tetrahydrofuran) was added dropwise to 196 ml of 1M LAH (lithium aluminum hydride) which was stirred and heated at 68°. The addition required 30 minutes and heating and stirring were continued for 2 hours. TLC in cyclohexane-ethyl acetate (1:1) and CHCl3MeOH (9:1) showed that the reaction was complete. The reaction was cooled to 0° and a total of 200 ml of water was continuously added. After being stirred for 15 minutes, the mixture was filtered and the solid was washed with THF. The combined filtrates were concentrated to yield 12.9 g (93%) of the title compound, RfCHCl3 -MeOH (9:1) 0.45.
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