Ammonium Chloride → HCID 15272401, compound
Reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[F:7])=[O:5].C([Li])CCC.CCCCCC.[CH2:27]([O:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:27]([O:34][C:35]1[CH:36]=[CH:37][C:38](/[CH:39]=[C:6](\[F:7])/[C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:41][CH:42]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of triethyl 2-fluoro-2-phosphonoacetate (4.90 g, 20.2 mmol) in tetrahydrofuran (40 mL) was stirred under a nitrogen atmosphere at 0° C., and 1.6 M n-butyl lithium/hexane solution (13.1 mL, 21.0 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 30 min and a solution of 4-benzyloxybenzaldehyde (4.29 g, 20.2 mmol) in tetrahydrofuran (20 mL) was added dropwise. The obtained mixture was stirred at room temperature for 3 hr and ice-cooled aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:97-20:80) to give the title compound (4.90 g, yield 81%) as a yellow oil.
Workup
- stirringThe obtained mixture was stirred at room temperature for 3 hr
- additionwas added
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:97-20:80)
Sources & evidence
- ORD record
- ord-0014073c41aa45b1bc4fad159a451c36
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07585880B2
Reaction notes
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