Ethyl Acetate → (R)-1-(benzo[b]thiophen-5-yl)-2-bromoethanol

HRID 1198224노트

반응식

HRID 1198224 반응식
[Br:1][CH2:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]2[S:9][CH:10]=[CH:11][C:7]=2[CH:6]=1)=[O:4].C(OCC)(=O)C>O1CCCC1>[S:9]1[CH:10]=[CH:11][C:7]2[CH:6]=[C:5]([C@@H:3]([OH:4])[CH2:2][Br:1])[CH:13]=[CH:12][C:8]1=2

참가 물질

4

반응물 2

HCID 8857Ethyl AcetateHCID 70605461-(1-Benzothiophen-5-yl)-2-bromo-1-ethanone

생성물 1

HCID 53833740(R)-1-(benzo[b]thiophen-5-yl)-2-bromoethanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-25 °C

실험 절차

A solution of 7.5 g of (+)-diisopinocamphenylchloroborane dissolved in 15 ml of tetrahydrofuran was cooled to -25° C. Thereto was added 4 g of 5-bromoacetylbenzo[b]thiophene. The resulting mixture was stirred for 4 hours at -20° C. to -15° C. The reaction mixture was added to a mixture of 80 ml of ethyl acetate and 80 ml of ice water. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure The residue thus obtained was purified by column chromatography (eluant: hexane:ethyl acetate=10:1) to obtain 3.8 of (R)-1-(benzo[b]thiophen-5-yl)-2-bromoethanol.

후처리

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure The residue
  5. customthus obtained
  6. customwas purified by column chromatography (eluant: hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-15ee4d60fc654426afbf0c5f0f09a5bf
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05280032

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