Water → (RS)-5-Benzyloxy-2-bromomethyl-2,3-dihydro-benzofuran

HRID 278431ノート

反応式

HRID 278431 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C(=O)C)=[C:11]([CH2:19][CH:20](Br)[CH2:21][Br:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].O.C(Cl)Cl>CCO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]2[O:15][CH:20]([CH2:21][Br:22])[CH2:19][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 6344Dichloromethane2 回HCID 10942334Sodium MethoxideHCID 54064179(RS)-Acetic acid 4-benzyloxy-2-(2,3-dibromo-propyl)-phenyl ester

生成物 1

HCID 22628347(RS)-5-Benzyloxy-2-bromomethyl-2,3-dihydro-benzofuran収率 83.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

(RS)-Acetic acid 4-benzyloxy-2-(2,3-dibromo-propyl)-phenyl ester (5.05 g, 11.3 mmol) was suspended in EtOH (50 ml) and sodium methoxide (620 mg, 11.3 mmol) added and the mixture stirred for 2 hr at ambient temperature. Distilled H2O (100 ml) and CH2Cl2 (100 ml) was then added and the organic phase separated. The aqueous phase was extracted with CH2Cl2 (100 ml) and the combined organic extracts washed with satd. NaCl solution (100 ml). After drying with Na2SO4, filtration and evaporation a yellow oil resulted which was chomatographed over SiO2 (Merck 230-400 mesh) with CH2Cl2 to afford 5-benzyloxy-2-(RS)-bromomethyl-2,3-dihydro-benzofuran as a yellow oil (3.0 g, 9.39 mmol, 83%), MS: m/e=318.0 (M+).

後処理

  1. customthe organic phase separated
  2. extractionThe aqueous phase was extracted with CH2Cl2 (100 ml)
  3. washthe combined organic extracts washed with satd
  4. dry with materialAfter drying with Na2SO4, filtration and evaporation a yellow oil
  5. customresulted which

出典と根拠

ORDレコード
ord-6926289ce4c249a2a2db0ce421ffb195
出典データセット
uspto-grants-2002_03
特許番号
US06359138B1

反応ノート

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