tert-Butyldimethylsilyl ethers of phenols: Their one-step conversion to benzyl or methyl ethers and utility in regioselective ortho lithiation

AK Sinhababu, M Kawase, RT Borchardt

文献索引：Sinhababu, Achintya K.; Kawase, Masami; Borchardt, Ronald T. Tetrahedron Letters, 1987 , vol. 28, # 36 p. 4139 - 4142

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被引用次数: 29

摘要

Summary: A new method for the one-step conversion of tert-butyldimethylsilyl ethers of phenols to benzyl or methyl ethers and the blocking effect of the tert-butyldimethylsilyloxy group in regioselective ortho lithiation are described ... 1 2 3: &Me; 4: R=Bn 5: FLTBDMS; 6: R=H ... The method is illustrated with the synthesis of 4 from 1. A mixture of 1 (2 mmol), anhydrous KF (4 mmol), PhCHZBr (2.4 mmol) in DMF (6 ml,) was stirred under an Ar atmosphere at 25°C for 2 h. The mixture ...