Water → Ethyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamate
Reaction equation
[H-].[Na+].[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O.[OH2:25]>O1CCCC1>[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[CH:9][C:7]([O:8][CH2:4][CH3:3])=[O:25]Participants
Procedure
Sodium hydride (oily, 60%, 2.40 g) was added little by little to a solution of triethyl phosphonoacetate (12.3 g) in tetrahydrofuran (200 ml) at 0° C., and the mixture was stirred at 10 minutes. Then, 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzaldehyde (14.7 g) was added, and the mixture was stirred at 0° C. for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate-hexane (1:3, v/v) gave crystals of ethyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamate (14.8 g, 81%). The crystals were recrystallized from ethanol. Colorless prisms, mp: 94-95° C.
Workup
- stirringthe mixture was stirred at 0° C. for 1 hour
- extractionextracted with ethyl acetate
- washThe ethyl acetate layer was washed with water
- dry with materialdried over magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- washThe fractions eluted with ethyl acetate-hexane (1:3
Sources & evidence
- ORD record
- ord-db686117f64945c1a75d56f8696e3a4f
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05965589
Reaction notes
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