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

HRID 862497ノート

反応式

HRID 862497 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 53833740(R)-1-(benzo[b]thiophen-5-yl)-2-bromoethanol収率 94.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-25 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-094ed0bb374040ef8e5030eb962d269c
出典データセット
uspto-grants-1998_02
特許番号
US05719150

反応ノート

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