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

HRID 278431노트

반응식

HRID 278431 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 6344Dichloromethane2회HCID 10942334Sodium MethoxideHCID 54064179(RS)-Acetic acid 4-benzyloxy-2-(2,3-dibromo-propyl)-phenyl ester

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

(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+).

후처리

  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

출처 및 근거

ORD 기록
ord-6926289ce4c249a2a2db0ce421ffb195
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06359138B1

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