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

HRID 71240Notes

Reaction equation

HRID 71240 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-46ab9832eba84abaaf56026f7db2aa05
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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