Hydrochloric Acid → 4-(Benzyloxy)-2-fluorocyclohexanol

HRID 271376Notes

Reaction equation

HRID 271376 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH:11]([F:16])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([OH:15])[CH:11]([F:16])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 59543141(2RS,4SR)-4-(Benzyloxy)-2-fluoro-cyclohexan-1-one

Product 1

HCID 595431264-(Benzyloxy)-2-fluorocyclohexanolYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A methanol (200 mL) solution of 4-(Benzyloxy)-2-fluorocyclohexanone (6.46 g, 29.1 mmol) was cooled in and ice bath under nitrogen. Sodium borohydride (1.66 g, 43.6 mmol) was added and the reaction aged 0.5 h. Hydrochloric acid (1 N) was slowly added after which methanol was removed under reduced pressure. Water was added and the resulting mixture was extracted with ethyl acetate (4×) and the combined organic extracts were washed with brine, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 4-(Benzyloxy)-2-fluorocyclohexanol as a pale oil (6.05 g, 93% yield).

Workup

  1. customthe reaction aged 0.5 h
  2. customwas removed under reduced pressure
  3. additionWater was added
  4. extractionthe resulting mixture was extracted with ethyl acetate (4×)
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e675ce7a3623434387129e22476f8004
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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