Facile Methods for the Direct Conversions of Aryl Acetates into the Corresponding Methoxymethyl Ethers or Silyl Ethers

References

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• Typical experimental procedure for the direct conversion of an ester-type protecting group into a silyl ether-type one is as follows: to a solution of sodium methoxide (28.7 mg, 0.531 mmol) in DMF (1 ml) was added 1-acetoxy-4-methylbenzene (57.6 mg, 0.384 mmol) in DMF (1.5 ml) under argon atmosphere. After stirring for 0.5 h at room temperature, t-butyldimethyls ilyl triflate (0.264 ml, 1.15 mmol) in DMF (1 ml) was added and stirring was continued for 1 h at room temperature. The mixture was then quenched with a phosphate buffer (pH 7). The organic materials were extracted with Et2O and the combined extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by thin-layer chromatography on silica gel to give 1-t-butyldimethylsilyloxy-4-methylbenzene (79.6 mg, 93%)
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