Sodium Fluoride → HCID 58288309, compound

HRID 1476132Notes

Reaction equation

HRID 1476132 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:56][CH2:34][CH3:37])=[O:54])=[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 difluoro(fluorosulphonyl)acetate were then slowly added dropwise, and the mixture was stirred at 110° C. for 60 min (caution: evolution of gas after about 30 min). After cooling to room temperature and addition of ethyl acetate and saturated aqueous sodium hydrocarbonate 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 (caution: 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-edaf20d78add47c99a71aa7e215520d2
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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