CC(C[AlH]CC(C)C)C.C[O:11][C:12](=O)[C:13]([CH3:22])([CH3:21])[CH2:14][O:15][CH:16]1[CH2:20][CH2:19][O:18][CH2:17]1.Cl>ClCCl>[CH3:21][C:13]([CH3:22])([CH2:14][O:15][CH:16]1[CH2:20][CH2:19][O:18][CH2:17]1)[CH2:12][OH:11]DIBAL (1.74 mL of a 1.0 M solution in hexanes) was added dropwise to a solution of 2,2-dimethyl-3-(tetrahydro-furan-3-yloxy)-propionic acid methyl ester (353 mg, 1.74 mmol) in dichloromethane (9.0 mL) at −78° C. After 2 h at this temperature, an additional equivalent of DIBAL was added and after 1 h the reaction was warmed to 0° C. After an additional 1 h at 0° C., 1.0 N HCl was added dropwise to quench the reaction. The reaction was warmed to room temperature and partitioned between dichloromethane and brine. The layers were separated and the aqueous layer extracted with dichloromethane. The combined organic layers were dried over Na2SO4 and concentrated to give an oil. Purification by flash column chromatography on silica gel using 50% ethyl acetate in hexanes provided 2,2-dimethyl-3-(tetrahydro-furan-3-yloxy)-propan-1-ol (250 mg, 82%) as a colorless oil.
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