Trifluoroacetic acid → HCID 1515504, compound

HRID 1917366Notes

Reaction equation

HRID 1917366 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].[CH2:8]([N:15]([CH2:20]OC)[Si](C)(C)C)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:23]1(=O)OC[CH:25]=[CH:24]1>C(=O)(O)[O-].[Na+]>[CH2:8]([N:15]1[CH2:20][C@H:2]2[C@H:24]([CH2:25][O:5][C:3]2=[O:4])[CH2:23]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 103412(5H)-FuranoneHCID 23062047Benzyl-methoxymethyl-trimethylsilanyl-amine

Product 1

HCID 1515504HCID 1515504, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Trifluoroacetic acid (0.136 mL) was added to a solution of N-benzyl-N-(methoxymethyl)-N-trimethylsilylamine (43.9 g, 185 mmol) and γ-crotonolactone (12.5 g, 176 mmol) in 1,2-dichloromethane (176 mL), and the mixture was stirred in a nitrogen atmosphere at room temperature for four hours. A saturated sodium bicarbonate solution (250 mL) was added to the reaction solution, followed by extraction with chloroform (200 mL×2). The organic layer was washed with brine (400 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→84:16→80:20→75:25→66:34→50:50) to give 37.1 g of the title compound.

Workup

  1. extractionfollowed by extraction with chloroform (200 mL×2)
  2. washThe organic layer was washed with brine (400 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→84:16→80:20→75:25→66:34→50:50)

Sources & evidence

ORD record
ord-a937074a5c2644d7bf6087d747e1ec93
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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