반응 #52064

반응 방정식

tert-butyl bromoacetate

3-hydroxybenzaldehyde

potassium tert-butoxide

tert-butanol

→

title compound

수율 36.5%

(3-Formyl-phenoxy)-acetic acid tert-butyl ester

수율 36.5%

용매

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction was stirred for 1 hour
2. 2
   기타was quenched with 200 mL of water
3. 3
   추출The product was extracted into EtOAc
4. 4
   세척the organic solution was washed with water
5. 5
   건조dried over MgSO4
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타Purification via flash chromatography on silica gel (9:1 hexanes:EtOAc)

실험 절차

To a solution of 3-hydroxybenzaldehyde (5.00 g, 40.9 mmol) in DMF (40 mL) was added 1M potassium tert-butoxide in tert-butanol (40.9 mL, 40.9 mmol). The reaction was stirred for 2 minutes and tert-butyl bromoacetate (6.61 mL, 40.9 mmol) was added. The reaction was stirred for 1 hour and was quenched with 200 mL of water. The product was extracted into EtOAc and the organic solution was washed with water, dried over MgSO4, filtered and concentrated in vacuo. Purification via flash chromatography on silica gel (9:1 hexanes:EtOAc) afforded the title compound as a clear oil (3.53 g). 1H NMR (400 MHz, CDCl3) δ 9.94 (s, 1H), 7.48 (m, 2H), 7.32 (s, 1H), 7.21 (m, 1H), 4.56 (s, 2H), 1.45 (s, 9H).

출처