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

HRID 29300ノート

反応式

HRID 29300 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 66778182Methyl 3-ethyl-1-benzofuran-2-carboxylate収率 38%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-575928b05e424320a7fca9255b2bb20c
出典データセット
uspto-grants-2008_09
特許番号
US07420001B2

反応ノート

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