Water → HCID 131736030, compound
Reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[F:17][C:18]([F:36])([C:32]([F:35])([F:34])[F:33])[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][O:28][CH2:29][O:30][CH3:31])[CH:22]=1)=O.O>C1COCC1>[F:17][C:18]([F:36])([C:32]([F:33])([F:34])[F:35])[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][O:28][CH2:29][O:30][CH3:31])[CH:22]=1)=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]Participants
Procedure
Under a nitrogen atmosphere, to a suspension of 60% sodium hydride (481 mg) in THF (15 mL) was added ethyl diethylphosphonoacetate (2.55 mL) at 0° C., and the mixture was stirred at room temperature for 5 min. To the obtained colorless solution was added 2,2,3,3,3-pentafluoro-1-(3-((methoxymethoxy)methyl)phenyl)propan-1-one (1.28 g) at room temperature, and the mixture was stirred at 0° C. for 30 min. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.37 g) as a pale-yellow oil.
Workup
- stirringthe mixture was stirred at 0° C. for 30 min
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-411a56d49ad241f88dc998f0e87ea788
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382188B2
Reaction notes
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