Water → HCID 67207151, compound

HRID 1476093Notes

Reaction equation

HRID 1476093 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[F:17][C:18]([F:32])([F:31])[C:19]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[C:23]([N+:28]([O-:30])=[O:29])[CH:22]=1)=O.O>C1COCC1.CN(C=O)C>[F:32][C:18]([F:17])([F:31])[C:19]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[C:23]([N+:28]([O-:30])=[O:29])[CH:22]=1)=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 67207883HCID 67207883, compound

Product 1

HCID 67207151HCID 67207151, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

10.9 g (48.5 mmol) of ethyl diethylphosphonoacetate were slowly added dropwise to an ice-cooled suspension of 1.86 g (60% in mineral oil, 46.4 mmol) of sodium hydride in a mixture of 70 ml of THF and 20 ml of DMF. After the addition had ended, the mixture was stirred at 0° C. for another 30 min, and 10.0 g (42.2 mmol) of 2,2,2-trifluoro-1-(4-fluoro-3-nitrophenyl) ethanone were then added. The reaction mixture was stirred at RT overnight and then added to water. The mixture was extracted three times with ethyl acetate, and the combined organic phases were concentrated under reduced pressure. The crude product gave, after chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 20:1 to 10:1), 9.23 g of the target product (71.2% of theory).

Workup

  1. temperaturecooled
  2. additionAfter the addition
  3. stirringThe reaction mixture was stirred at RT overnight
  4. extractionThe mixture was extracted three times with ethyl acetate
  5. concentrationthe combined organic phases were concentrated under reduced pressure

Sources & evidence

ORD record
ord-76a37e0c7e57408ab538192fb7434aef
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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