Ammonium Chloride → (1s,4s)-4-(3-Fluorophenyl)cyclohexanol

HRID 1095246Notes

Reaction equation

HRID 1095246 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[H][H].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[F:3][C:4]1[CH:5]=[C:6]([CH:10]2[CH2:11][CH2:12][CH:13]([OH:16])[CH2:14][CH2:15]2)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 189531424-(3-Fluorophenyl)cyclohexanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 57368435(1s,4s)-4-(3-Fluorophenyl)cyclohexanolYield 85.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (9.8 g) and THF (100 ml) were put in a reaction vessel under a nitrogen atmosphere, and cooled to 0° C. The compound (19) (47.2 g) dissolved in THF (100 ml) was added dropwise thereto, with caution in the evolution of hydrogen gas, and the mixture was stirred for 3 hours. A saturated aqueous solution of ammonium chloride (400 ml) and ethyl acetate (400 ml) were added and mixed thereto. The mixture was then allowed to stand until it had separated into organic and aqueous phases, and an extractive operation to an organic phase was carried out. The organic phase was fractionated, and washed with brine, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified with a fractional operation by means of column chromatography using a mixed solvent of toluene and ethyl acetate (toluene: ethyl acetate=10:1 by volume) as an eluent and silica gel as a stationary phase powder, and dried, giving 40.9 g of 4-(3-fluorophenyl)cyclohexanol (20). The yield based on the compound (19) was 85.7%.

Workup

  1. additionwas added dropwise
  2. additionmixed
  3. customhad separated into organic and aqueous phases
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe solution was concentrated under reduced pressure
  7. customthe residue was purified with a fractional operation by means of column chromatography
  8. customsilica gel as a stationary phase powder, and dried

Sources & evidence

ORD record
ord-9dcc7c55b28b4a5d84309e5341f97ed3
Source dataset
uspto-grants-2012_03
Patent number
US08137583B2

Reaction notes

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