Trifluoroacetic acid → HCID 6558968, compound

HRID 1917372Notes

Reaction equation

HRID 1917372 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]([C:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1)=[O:11].[CH2:18]([N:25]([CH2:31]OC)[CH2:26][Si](C)(C)C)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+]>ClCCCl>[CH3:8][O:9][C:10]([C@@:12]12[CH2:31][N:25]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26][C@@H:17]1[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 87647Methyl cyclohex-1-ene-1-carboxylateHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 516892Sodium Bicarbonate

Product 1

HCID 6558968HCID 6558968, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A catalytic amount of trifluoroacetic acid was added to a solution of 1-cyclohexene-1-carboxylic acid methyl ester (25.0 g, 178 mmol) and N-benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine (46.6 g, 196 mmol) in 1,2-dichloroethane (178 mL) at room temperature, and the mixture was stirred at room temperature for two hours. A saturated sodium bicarbonate solution (200 mL) was added to the reaction solution, followed by extraction with chloroform (150 mL×1, 100 mL×1). The organic layer was washed with brine (450 ml) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→90:10→85:15→75:25) to give 21.3 g of the title compound.

Workup

  1. extractionfollowed by extraction with chloroform (150 mL×1, 100 mL×1)
  2. washThe organic layer was washed with brine (450 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→90:10→85:15→75:25)

Sources & evidence

ORD record
ord-23e35b0104d549c28d7ede4067ad0a51
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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