Sodium hydride → Methyl (2E)-3-(1-methyl-1H-imidazol-4-yl)-2-propenoate

HRID 540410Notes

Reaction equation

C(OP([CH2:9][C:10]([O:12][CH3:13])=[O:11])(OCC)=O)C.[H-].[Na+].[CH3:16][N:17]1[CH:21]=[C:20]([CH:22]=O)[N:19]=[CH:18]1>O1CCCC1>[CH3:16][N:17]1[CH:21]=[C:20](/[CH:22]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])[N:19]=[CH:18]1

Participants

Conditions

Temperature: 0 °C

Procedure

1 ml (5.5 mmol) of methyl diethylphosphonoacetate are added to a suspension of 220 mg (5.5 mmol) of sodium hydride at 60% in 5 ml of tetrahydrofuran cooled to 0° C. After stirring for 1 h, 500 mg (4.5 mmol) of 1-methyl-1H-imidazole-4-carbaldehyde are added and the mixture is stirred for 4 hours at ambient temperature and then hydrolysed with water and extracted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over magnesium sulphate, filtered and evaporated. The product obtained is precipitated from heptane and filtered. 430 mg of methyl (E)-3-(1-methyl-1H-imidazol-4-yl)acrylate are obtained in the form of a yellow powder with a yield of 57%.

Workup

stirringthe mixture is stirred for 4 hours at ambient temperature
extractionhydrolysed with water and extracted with ethyl acetate
washThe organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate
dry with materialdried over magnesium sulphate
filtrationfiltered
customevaporated
customThe product obtained
customis precipitated from heptane
filtrationfiltered

Sources & evidence

ORD record: ord-5e3b943bd15746d69f4f64761bc1fcd9
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871187B2

Reaction notes

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