Methanol → 5-(trifluoromethyl)-2,3-dihydro-1H-inden-1-ol

HRID 2178768노트

반응식

HRID 2178768 반응식
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[BH4-].[Na+].CO>C1COCC1>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([OH:12])[CH2:7][CH2:6]2

참가 물질

5

반응물 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 121749875-(Trifluoromethyl)indan-1-one

생성물 1

HCID 248204735-(trifluoromethyl)-2,3-dihydro-1H-inden-1-ol수율 107.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-(trifluoromethyl)indan-1-one (0.7 g, 3 mmol) in THF (5 mL) cooled in an ice bath was added sodium borohydride (0.1 g, 3 mmol) followed by MeOH (1 mL). After being stirred for 30 min, the reaction was quenched with aqueous NaHCO3. The resulting solution was extracted with EtOAc twice. The extracts were washed with brine, dried (MgSO4), filtered and concentrated. The crude material was purified by flash chromatography on silica eluting with 20% EtOAc/hexane to afford the desired product (0.65 g, 92%) as an oil. LC/MS calculated for C10H9F3O: (M+H)+203; found 185.1 (M+H—H2O)+.

후처리

  1. customthe reaction was quenched with aqueous NaHCO3
  2. extractionThe resulting solution was extracted with EtOAc twice
  3. washThe extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography on silica eluting with 20% EtOAc/hexane

출처 및 근거

ORD 기록
ord-4e80906e6f7e4d768ab505c9ece95f6e
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067921B2

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