Water → HCID 86672783, compound

HRID 1755064Notes

Reaction equation

HRID 1755064 reaction equation
[F:1][C:2]([Si](C)(C)C)([F:7])[C:3]([F:6])([F:5])[F:4].[CH2:12]([O:19][C:20]([CH:22]1[CH2:27][CH2:26][CH:25]([CH2:28]OS(C(F)(F)F)(=O)=O)[CH2:24][CH2:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[F-].C[N+](C)(C)C.O>COCCOC>[CH2:12]([O:19][C:20]([CH:22]1[CH2:27][CH2:26][CH:25]([CH2:28][C:2]([F:7])([F:1])[C:3]([F:6])([F:5])[F:4])[CH2:24][CH2:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67803Tetramethylammonium fluorideHCID 2760820(Pentafluoroethyl)trimethylsilaneHCID 86672784HCID 86672784, compound

Product 1

HCID 86672783HCID 86672783, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

(Pentafluoroethyl)trimethylsilane (105 mg, 0.548 mmol) was added to a solution of 4-trifluoromethanesulfonyloxymethyl-cyclohexanecarboxylic acid benzyl ester (cis:trans=4:1) (67.0 mg, 0.176 mmol) in DME (0.88 ml) at −30° C., and tetramethylammonium fluoride (21 mg, 0.22 mmol) was then added at −30 to −27° C. over one hour. The mixture was stirred for four hours while warming from −30° C. to 0° C. and further stirred at 0° C. for one hour. Water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=150/1) to give 4-(2,2,3,3,3-pentafluoro-propyl)-cyclohexanecarboxylic acid benzyl ester (cis:trans=11:1) (11.4 mg, 18%).

Workup

  1. temperaturewhile warming from −30° C. to 0° C.
  2. stirringfurther stirred at 0° C. for one hour
  3. extractionfollowed by extraction with dichloromethane
  4. dry with materialThe organic layer was then dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=150/1)

Sources & evidence

ORD record
ord-3f2d5529bd734dcc953e9240851e41cb
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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