Methyl 3,3-bis[(tert-butyldimethylsiloxy)methyl]acrylate → 3,3-Bis[(tert-butyldimethylsiloxy)methyl]-2-propen-1-ol

Beteiligte Stoffe

Reaktionsschritte

A solution of 5a (11.24 g, 30 mmol) in CH2Cl2 (100 mL) was cooled to -60° C. and treated dropwise with a solution of diisobutylaluminum hydride in CH2Cl2 (1.0M, 40 mL). The reaction mixture was quenched with saturated potassium sodium tartrate tetrahydrate and warmed to room temperature. The aqueous layer was extracted with CH2Cl2, and the combined organic layer was washed with water and brine. The organic layer was dried (NaSO4) and concentrated. The residue was purified by flash column chromatography over silica gel with hexane:EtOAc (5:1) as eluant to give 6a (9.77 g, 94%) as an oil: IR (neat) 3357, 1471 cm-1 ; 1H NMR (CDCl3) δ 0.05 and 0.06 (s, 6 H, SiCH3), 0.88 and 0.89 (s, 9 H, C(CH3)3), 1.86 (br s, 1 H, OH), 4.14 (br s, 2 H, CH2OH), 4.20 (m, 4 H, CH2OSi), 5.80 (m, 1 H, =CH); 13C NMR (CDCl3) δ -1.95, 18.19, 18.33, 25.62, 25.79, 25.88, 58.50, 59.24, 64.75, 125.47, 140.81. Anal. Calcd for C17H38O3Si2 : C, 58.90; H: 11.05. Found: C, 59.00; H, 11.00.

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