Hydrochloric Acid → Methyl 3-ethyl-1-benzofuran-2-carboxylate

HRID 29300노트

반응식

HRID 29300 반응식
[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=O)[CH2:13][CH3:14].C[O-].[Na+].Cl>CO.O>[CH3:1][O:2][C:3]([C:4]1[O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:12]=1[CH2:13][CH3:14])=[O:16]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 24701002(2-Propionyl-phenoxy)-acetic acid methyl ester

생성물 1

HCID 66778182Methyl 3-ethyl-1-benzofuran-2-carboxylate수율 38%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

(2-Propionyl-phenoxy)-acetic acid methyl ester (432 mg, 1.94 mmol, 1 eq.) was added to a solution of sodium methoxide (105 mg, 0.94 mmol, 1 eq.) in methanol (10 mL) and the reaction was heated at 60° C. for 4 h. The reaction was acidified using 1N HCl, diluted with water, extracted twice with ethyl acetate, and the combined organic layers were washed with saturated aqueous NaHCO3. The aqueous layers were extracted with ethyl acetate. The organic layers were combined, dried over magnesium sulfate, and concentrated in vacuo. 3-Ethyl-benzofuran-2-carboxylic acid methyl ester is obtained in 38% yield after flash column chromatography purification (1-5% ethyl acetate/hexanes). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.2 (t, J=7.6 Hz, 3 H) 3.1 (q, J=7.6 Hz, 2 H) 3.9 (s, 3 H) 7.4 (m, 1 H) 7.5 (m, 1 H) 7.7 (m, 1 H) 7.9 (dd, J=7.8, 0.8 Hz, 1 H).

후처리

  1. extractionextracted twice with ethyl acetate
  2. washthe combined organic layers were washed with saturated aqueous NaHCO3
  3. extractionThe aqueous layers were extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-575928b05e424320a7fca9255b2bb20c
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420001B2

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