Sodium Bicarbonate → (2RS,4SR)-4-(Benzyloxy)-2-fluoro-cyclohexan-1-one

HRID 1970983Notes

Reaction equation

HRID 1970983 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([O:15][Si](C(C)(C)C)(C)C)=[CH:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[B-](F)(F)(F)[F:24].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH:11]([F:24])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724933SelectfluorHCID 68669646{[4-(Benzyloxy)cyclohex-1-en-1-yl]oxy}(tert-butyl)dimethylsilane

Product 1

HCID 59543141(2RS,4SR)-4-(Benzyloxy)-2-fluoro-cyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of {[4-(benzyloxy)cyclohex-1-en-1-yl]oxy}(tert-butyl)dimethylsilane (11.5 g, 36.1 mmol) in DMF (75 mL) was added Selectfluor (25.6 g, 72.2 mmol) in small portions at 0° C. After completion of the reaction, the mixture was poured into 5% sodium bicarbonate solution. The resulting mixture was extracted with EtOAc, and the combined organics were washed with brine, dried, and concentrate to afford the title compound.

Workup

  1. customAfter completion of the reaction
  2. extractionThe resulting mixture was extracted with EtOAc
  3. washthe combined organics were washed with brine
  4. customdried
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-d906d72176fa4e598e50632a6127ac01
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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