Acetone cardice → 2-(6-bromo-5-fluoro-1H-indol-1-yl)ethanol

HRID 331044노트

반응식

HRID 331044 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][C:12](OC)=[O:13])=[CH:4][C:3]=1[F:16].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(=O)=O.CC(C)=O>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][CH2:12][OH:13])=[CH:4][C:3]=1[F:16]

참가 물질

5

반응물 3

HCID 18522661Acetone cardiceHCID 21226445Aluminium lithium hydrideHCID 71090281Methyl 2-(6-bromo-5-fluoro-1H-indol-1-yl)acetate

생성물 1

HCID 710904052-(6-bromo-5-fluoro-1H-indol-1-yl)ethanol수율 96.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Methyl 2-(6-bromo-5-fluoro-1H-indol-1-yl)acetate (D77) (10.2 g, 35.7 mmol) was dissolved up in 81 mL of THF and cooled in a cardice/acetone bath before the addition of LiAlH4 (2N in THF solution) (17.83 mL, 35.7 mmol). The reaction mixture was left to stir in the cardice/acetone bath for 30 mins. Whilst still in the bath the reaction mixture was quenched by the dropwise addition of saturated sodium sulfate aqueous solution. The solid formed was filtered off and washed with ethyl acetate. The filtrate was washed with brine. The organic layer was passed through a hydrophobic frit and concentrated to afford title compound (8.852 g). LCMS (A): m/z (M+H)+ 258/260, C10H9BrFNO requires 257/259 (acidic).

후처리

  1. waitThe reaction mixture was left
  2. customWhilst still in the bath the reaction mixture was quenched by the dropwise addition of saturated sodium sulfate aqueous solution
  3. customThe solid formed
  4. filtrationwas filtered off
  5. washwashed with ethyl acetate
  6. washThe filtrate was washed with brine
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-94067bdb7f104c4787aaec2c082cac26
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877742B2

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