1-(3-Fluorophenyl)cyclohexanecarboxylic acid → (1-(3-Fluorophenyl)cyclohexyl)methanol

HRID 71240노트

반응식

HRID 71240 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:8]2([C:14](O)=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 7361321-(3-Fluorophenyl)cyclohexanecarboxylic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 66685136(1-(3-Fluorophenyl)cyclohexyl)methanol수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of 1-(3-fluorophenyl)cyclohexanecarboxylic acid (0.8 g, 3.60 mmol) in THF (10 mL) at 0° C. was added 2M lithium aluminum hydride (2.500 mL, 5.0 mmol) in THF dropwise and the mixture was stirred at 0° C. for 1.5 hrs. The reaction was quenched with Na2SO4.10H2O and stirred for 0.5 hrs. The reaction mixture was filtered through Celite and washed with EtOAc. The filtrate was washed with 1N HCl followed by 1N NaOH and brine. The EtOAc layer was dried over Na2SO4 and evaporated to give (1-(3-fluorophenyl)cyclohexyl)methanol (675 mg, 3.24 mmol, 90% yield) as an oil. 1H NMR (400 MHz, CCl3D) δ ppm 7.33 (1H, td, J=8.02, 6.37 Hz), 7.16 (1H, d, J=7.91 Hz), 7.09 (1H, dt, J=11.26, 2.17 Hz), 6.89-6.96 (1H, m), 3.50 (2H, s), 2.10 (2H, dd, J=12.85, 3.84 Hz), 1.30-1.66 (9H, m).

후처리

  1. customThe reaction was quenched with Na2SO4.10H2O
  2. stirringstirred for 0.5 hrs
  3. filtrationThe reaction mixture was filtered through Celite
  4. washwashed with EtOAc
  5. washThe filtrate was washed with 1N HCl
  6. dry with materialThe EtOAc layer was dried over Na2SO4
  7. customevaporated

출처 및 근거

ORD 기록
ord-46ab9832eba84abaaf56026f7db2aa05
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822510B2

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