Water → HCID 118308682, compound

HRID 923482Notes

Reaction equation

HRID 923482 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=[CH2:14])=[O:4].C[N+]1([O-])CC[O:21]CC1.C1COCC1.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH2:37]>O=[Os](=O)(=O)=O>[OH:37][CH:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][NH:5][C:3](=[O:4])[C:2]([F:15])([F:16])[F:1])[CH2:14][OH:21]

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 118308724HCID 118308724, compound

Product 1

HCID 118308682HCID 118308682, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a mixture of 1.7 g of 2,2,2-trifluoro-N-(2-vinylbenzyl)acetamide, 1.31 g of 4-methylmorpholine 4-oxide, 43 ml of THF, and 17 ml of water was added 1.85 ml of a 2.5% aqueous tetraoxoosmium solution, followed by stirring at room temperature for 16 hours. To the reaction mixture was added a 10% aqueous sodium thiosulfate solution, followed by stirring at room temperature, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and washed with anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure to obtain 1.94 g of N-[2-(1,2-dihydroxyethyl)benzyl]-2,2,2-trifluoroacetamide.

Workup

  1. stirringby stirring at room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. washwashed with anhydrous magnesium sulfate
  5. customthe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-a095f3cfb1d044b19e9accb78d8fdccc
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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