反应详情

NaH (3.5 g of a 60% suspension, 87.4 mmol) is added to a solution of phenol (8.23 g, 87.4 mmol) in THF (100 mL) at room temperature. 2-Methanesulfonyl-pyrimidine-4-carboxylic acid methyl ester, 13, (6.3 g, 29.1 mmol) is dissolved in THF (60 mL) and added dropwise to the solution of phenol. The reaction is allowed to stir for 12 hours then quenched by the addition of saturated aqueous NH4Cl. The aqueous phase is extracted with methylene chloride and the combined organic layers are dried, filtered, and concentrated in vacuo to afford a crude oil which is purified over silica (ethyl acetate/hexane 2:3) to afford 1.72 g (25% yield) of the desired product as a white solid.

1. customthen quenched by the addition of saturated aqueous NH4Cl
2. extractionThe aqueous phase is extracted with methylene chloride
3. customthe combined organic layers are dried
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customto afford a crude oil which
7. customis purified over silica (ethyl acetate/hexane 2:3)