Lithium borohydride → (4-Cyclopentyl-3-(trifluoromethyl)phenyl)methanol

HRID 534257

반응식

HRID 534257 반응식
[CH:1]1([C:6]2[CH:15]=[CH:14][C:9]([C:10](OC)=[O:11])=[CH:8][C:7]=2[C:16]([F:19])([F:18])[F:17])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Li+]>O1CCOCC1>[CH:1]1([C:6]2[CH:15]=[CH:14][C:9]([CH2:10][OH:11])=[CH:8][C:7]=2[C:16]([F:17])([F:18])[F:19])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 11097668Methyl 4-cyclopentyl-3-(trifluoromethyl)benzoate

생성물 1

HCID 58020942(4-Cyclopentyl-3-(trifluoromethyl)phenyl)methanol수율 16.5%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of methyl 4-cyclopentyl-3-(trifluoromethyl)benzoate (8.16 g, 30.0 mmol) in 1,4-dioxane (200 mL) was added lithium borohydride solution (2 M in tetrahydrofuran, 30.0 mL, 59.9 mmol). The mixture was heated under reflux for 2.5 h. The mixture was allowed to cool to room temperature and carefully quenched with 1 N aqueous HCl solution to pH 5. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography to give the title compound as a colorless oil (1.21 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.56-1.63 (m, 2H), 1.66-1.77 (m, 2H), 1.81-1.91 (m, 2H), 2.03-2.15 (m, 2H), 3.37 (quintet, J=8.00 Hz, 1H), 4.71 (d, J=4.29 Hz, 2H), 7.45-7.47 (m, 1H), 7.49 (d, J=1.14 Hz, 1H), 7.60 (s, 1H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2.5 h
  3. customcarefully quenched with 1 N aqueous HCl solution to pH 5
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-33f821e2fbac472fa87af449b51668fa
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853419B2

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