Triethyl phosphonoacetate → HCID 54164066, compound
Reaction equation
CC(C)([O-])C.[K+].C(OP([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(OCC)=O)C.[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([O:30][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:26]([CH:29]=1)[CH:27]=O.C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([O:30][CH2:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[C:26]([CH:29]=1)[CH:27]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]Participants
Procedure
In an argon gas stream, 3.49 g of potassium t-butoxide was added to a solution of 8.36 g of ethyl diethylphosphonoacetate in 100 ml of tetrahydrofuran under ice-cooling. The obtained mixture was then stirred at the same temperature for 1 hour. Next, a solution of 5.40 g of 5-chloro-2-(2-phenylethoxy)benzaldehyde in 30 ml of tetrahydrofuran was added dropwise to the reaction mixture and the resulting mixture was stirred at the same temperature for 1 hour and then at room temperature for 19 hours. After adding 30 ml of a saturated aqueous solution of sodium hydrogencarbonate, the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, 11.56 g of crude ethyl 5-chloro-2-(2-phenylethoxy)cinnamate was obtained. Thus compound was not purified any more but used in the subsequent reaction as such.
Workup
- temperaturecooling
- stirringthe resulting mixture was stirred at the same temperature for 1 hour
- waitat room temperature for 19 hours
- extractionthe mixture was extracted with ethyl acetate
- dry with materialdried over anhydrous magnesium sulfate
- customAfter evaporation of the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-828f0629d46641b48a09095f1074ce7e
- Source dataset
- uspto-grants-1996_02
- Patent number
- US05495046
Reaction notes
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