[Li]CCCC.[Si:6]([C:13]1[O:14][CH:15]=[CH:16][C:17]=1[CH2:18][OH:19])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[Cl-].[Li+].CN(C)[CH:24]=[O:25]>CCCCCC.C(COC)OC>[Si:6]([C:13]1[O:14][CH:15]=[C:16]([CH:24]=[O:25])[C:17]=1[CH2:18][OH:19])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]
n-BuLi (a 1.6M solution in hexane; 2.7 ml, 4.28 mmol) was added dropwise to a solution of 3-(2-tert-butyldimethylsilyl-furylmethanol (430 mg, 2.0 mmol) in dimethoxyethane (5 ml) at -78 degrees C. under argon. After stirring at 0 degrees C. for 15 minutes, lithium chloride (860 mg, 20.4 mmol), followed by N,N-dimethylformamide (0.35 ml, 4.48 mmol) was added. Stirring continued at 0 degrees C. for 16 hours and the mixture was quenched with ammonium chloride. Extraction with ethyl acetate and evaporation of the dried (magnesium sulfate) extracts gave a solid, which was recrystallized from hexane to give the titled aldehyde.
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