반응 #648963

반응 방정식

sodium hydride

tert-butyl 2-chloro-5-(2-hydroxyethyl)benzoate

iodomethane

→

title compound

tert-Butyl 2-chloro-5-(2-methoxyethyl)benzoate

용매

THF

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   workup.ADDITIONwas added
3. 3
   기타After carefully quenching with sat. aq. NaHCO3
4. 4
   추출the resulting mixture was extracted with ether
5. 5
   세척The combined organic extracts were washed with brine
6. 6
   건조dried over MgSO4
7. 7
   여과filtered
8. 8
   기타Concentration of the filtrate in vacuo afforded a cloudy oil
9. 9
   기타Purification of the crude product
10. 10
    기타thus obtained by way of flash chromatography (SiO2, Hex→85:15 (v/v) Hex:EtOAc)

실험 절차

To a suspension of sodium hydride (60% w/w dispersion in oil, 2 eq.) in anhydrous THF (0.23 M) was added tert-butyl 2-chloro-5-(2-hydroxyethyl)benzoate from the previous step (1 eq.). The reaction mixture was heated at reflux for 30 min before iodomethane (7.9 eq.) was added. After carefully quenching with sat. aq. NaHCO3, the resulting mixture was extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a cloudy oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→85:15 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

출처