Sodium Fluoride → HCID 58288309, compound

HRID 2402359Notes

Reaction equation

HRID 2402359 reaction equation
[F:1][C:2]([F:20])([F:19])[C@H:3]([CH3:18])[CH:4]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[CH2:17])=[CH:12][CH:11]=1)C(OCC)=O.[F-].[Na+].C(C1C=C(C)C=C([C:34]([CH3:37])(C)C)C=1O)(C)(C)C.[F:39][C:40]([F:52])(S(F)(=O)=O)C(O[Si](C)(C)C)=O.[C:53](=[O:56])(O)[O-:54].[Na+]>C(OCC)(=O)C>[F:39][C:40]1([F:52])[CH2:17][CH:16]1[C:13]1[CH:12]=[CH:11][C:10]([CH:4]([C@@H:3]([CH3:18])[C:2]([F:1])([F:19])[F:20])[C:53]([O:54][CH2:34][CH3:37])=[O:56])=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 5235Sodium FluorideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 516892Sodium BicarbonateHCID 2778022Trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetateHCID 58288259HCID 58288259, compound

Product 1

HCID 58288309HCID 58288309, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.58 g (5.52 mmol) of ethyl (3R)-4,4,4-trifluoro-3-methyl-2-(4-vinylphenyl)butanoate, 23 mg (0.55 mmol) of sodium fluoride and 24 mg (0.11 mmol) of 2,6-di-tert-butyl 4-methylphenol were heated to 110° C. and stirred for 5 minutes. 1.9 ml (9.38 mmol) of trimethylsilyl 2,2-difluoro-2-(fluorosulphonyl)acetate were then slowly added dropwise, and the mixture was stirred at 110° C. for 60 min (careful: evolution of gas after about 30 min). After cooling to room temperature and addition of ethyl acetate and saturated aqueous sodium bicarbonate solution, the organic phase was separated off, dried over magnesium sulphate, filtered and concentrated to dryness. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/-dichloromethane 4:1). This gave 1.5 g of the title compound (81% of theory).

Workup

  1. stirringthe mixture was stirred at 110° C. for 60 min (careful: evolution of gas after about 30 min)
  2. customthe organic phase was separated off
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/-dichloromethane 4:1)

Sources & evidence

ORD record
ord-c7c2b3a2da0e498c9fc708fb22dec274
Source dataset
uspto-grants-2014_08
Patent number
US08796335B2

Reaction notes

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