2-Methoxypropene → HCID 118308735, compound

HRID 923488Notes

Reaction equation

HRID 923488 reaction equation
[OH:1][CH:2]([C:5]1[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=1[CH2:7][NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH2:3][OH:4].CO[C:21]([CH3:23])=[CH2:22].O.CC1C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CC(C)=O>[CH3:22][C:21]1([CH3:23])[O:1][CH:2]([C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[CH2:7][NH:8][C:9](=[O:14])[C:10]([F:12])([F:13])[F:11])[CH2:3][O:4]1

Participants

6

Reactant 4

HCID 83002-MethoxypropeneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 118308682HCID 118308682, compound

Product 1

HCID 118308735HCID 118308735, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 1.93 g of N-[2-(1,2-dihydroxyethyl)benzyl]-2,2,2-trifluoroacetamide and 20 ml of acetone were added 1.1 ml of 2-methoxyprop-1-ene and 140 mg of 4-methylbenzenesulfonic acid monohydrate under ice-cooling, followed by stirring at room temperature for 2 hours. To the reaction mixture was added an aqueous sodium hydrogen carbonate solution under ice-cooling, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2.2 g of N-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)benzyl]-2,2,2-trifluoroacetamide.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. customthe solvent was then evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9b13dee5c1fe472f9402e745c2119cfb
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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