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

HRID 71240ノート

反応式

HRID 71240 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 66685136(1-(3-Fluorophenyl)cyclohexyl)methanol収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-46ab9832eba84abaaf56026f7db2aa05
出典データセット
uspto-grants-2014_09
特許番号
US08822510B2

反応ノート

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