反应详情

Tert-butyldimethylsilyl chloride (24.1 g) was added to a mixture of 4-hydroxybenzaldehyde (17.8 g), imidazole (19.8 g) and N,N-dimethylformamide (100 ml). After stirring at room temperature for 2 hours, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was dissolved in tetrahydrofuran (300 ml) and methanol (40 ml), and then sodium borohydride (11.1 g) was added in portions at 0° C. After stirring for 30 minutes, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain 4-(tert-butyldimethylsilyloxy)benzylalcohol (27.7 g, yield 79%) as a colorless oil from an ethyl acetate-hexane (1:4, v/v)-eluted fraction.

1. extractionextracted with ethyl acetate
2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
3. dry with materialdried (MgSO4)
4. concentrationconcentrated
5. dissolutionThe residue was dissolved in tetrahydrofuran (300 ml)
6. additionmethanol (40 ml), and then sodium borohydride (11.1 g) was added in portions at 0° C
7. stirringAfter stirring for 30 minutes
8. additionwater was added
9. extractionextracted with ethyl acetate
10. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
11. dry with materialdried (MgSO4)
12. concentrationconcentrated