Sodium hydride → HCID 22097916, compound
Reaction equation
C(OP([CH:9]([F:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[CH3:16][C:17]1([CH3:32])[CH:19](/[CH:20]=C(\Br)/C(OCCC)=O)[CH:18]1[C:29]([OH:31])=[O:30].[H-].[Na+].P(O)(O)([O-])=O.[Na+]>COCCOC>[CH3:16][C:17]1([CH3:32])[CH:19](/[CH:20]=[C:9](/[F:15])\[C:10](=[O:11])[O:12][CH2:13][CH3:14])[CH:18]1[C:29]([OH:31])=[O:30]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
A solution of 7.7 g of ethyl diethyl-phosphono-fluoroacetate (prepared by process of Ann. Chem., 1964, p. 6741), 60 ml of 1,2-dimethoxyethane and 4 g of (1R, trans) 2,2-dimethyl-3-formyl-cyclopropane-carboxylic acid was added over 30 minutes at 2° to 10° C. to a suspension of 2.6 g of a 60% sodium hydride in oil suspension and 60 ml of 1,2-dimethoxyethane and the mixture was stirred at 5° C. for 15 minutes, and then at room temperature for 3 hours. The resulting solution was poured into aqueous monosodium phosphate solution at 5° C. and the mixture was stirred for 10 minutes. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried and evaporated to dryness at 40° C. under reduced pressure to obtain 6.5 g of an oil residue. The latter was chromatographed over silica gel and was eluted with a 70-30-1 hexane-ethyl acetate-acetic acid mixture to obtain 4 g of (1R,trans) 2,2-dimethyl-3(E)-[2-fluoro-3-oxo-3-ethoxypropenyl]-cyclopropane-1-carboxylic acid
Workup
- waitat room temperature for 3 hours
- stirringthe mixture was stirred for 10 minutes
- extractionThe mixture was extracted with ethyl acetate
- washthe organic phase was washed with water
- customdried
- customevaporated to dryness at 40° C. under reduced pressure
Sources & evidence
- ORD record
- ord-2b2e8cdea1794c64ba0aa8beb516aa55
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04808749
Reaction notes
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