Ethyl Acetate → HCID 69052429, compound

HRID 1792965Notes

Reaction equation

HRID 1792965 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:16])[CH2:7]P(OCC)(OCC)=O)[CH3:4].O[CH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:25]=2)[C:20](=[O:31])[N:19]1[CH2:32][C:33]([F:36])([F:35])[F:34].CC(=O)OCC>COCCOC>[CH2:3]([O:5][C:6](=[O:16])[CH2:7][CH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([S:27]([CH3:30])(=[O:28])=[O:29])[CH:25]=2)[C:20](=[O:31])[N:19]1[CH2:32][C:33]([F:34])([F:36])[F:35])[CH3:4]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 22025447HCID 22025447, compound

Product 1

HCID 69052429HCID 69052429, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

0.56 g of a 60% suspension of NaH in mineral oil were suspended in 20 ml of DME. Afterwards, 2.8 ml of (diethoxy-phosphoryl)-acetic acid ethyl ester were added dropwise at ambient temperature and the mixture stirred for 1 h at that temperature. A solution prepared of 3-hydroxy-5-methanesulfonyl-2-(2,2,2-trifluoro-ethyl)-2,3-dihydro-isoindol-1-one using 30 ml of DME was then added and the mixture was heated up to reflux. The mixture was refluxed for 4 h and then allowed to cool to ambient temperature. 300 ml of EA were added and the mixture was washed 3 times using 100 ml of saturated aqueous NaHCO3 solution each time. The aqueous layer was then extracted twice using 100 ml of EA each time. The combined EA layers were dried over Na2SO4 and the solvent was removed in vacuo. Chromatography on silica gel using MTB yielded 1.1 g of a colorless oil (Rf (MTB)=0.40; MS (DCI): 380 (M+1)+).

Workup

  1. additionwas then added
  2. temperaturethe mixture was heated up
  3. temperatureto reflux
  4. temperatureThe mixture was refluxed for 4 h
  5. washthe mixture was washed 3 times
  6. extractionThe aqueous layer was then extracted twice
  7. dry with materialThe combined EA layers were dried over Na2SO4
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a67c2ef8ada640688782f3602f512067
Source dataset
uspto-grants-2006_07
Patent number
US07078428B2

Reaction notes

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