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

HRID 862497노트

반응식

HRID 862497 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-bromoethanol수율 94.3%

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 g 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
  5. customThe residue thus obtained
  6. customwas purified by column chromatography (eluant: hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-094ed0bb374040ef8e5030eb962d269c
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05719150

반응 노트

불러오는 중…