Sodium hydride → ethyl (E)-3-(4-iodo-3-propoxyphenyl)-2-methylacrylate

HRID 390648Notes

Reaction equation

[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[CH3:7])=[O:5].[H-].[Na+].[I:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][C:20]=1[O:27][CH2:28][CH2:29][CH3:30].[Cl-].[NH4+]>O1CCCC1>[I:18][C:19]1[CH:26]=[CH:25][C:22](/[CH:23]=[C:6](\[CH3:7])/[C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:21][C:20]=1[O:27][CH2:28][CH2:29][CH3:30]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1.8 g (7.7 mmol) of triethyl 2-phosphonopropionate in 25 mL of tetrahydrofuran is added to a suspension of 310 mg (7.7 mmol) of 60% sodium hydride in oil, precooled to 0° C. After stirring at 0° C. for 15 minutes, a solution of 1.5 g (5.2 mmol) of 4-iodo-3-propoxybenzaldehyde in 10 mL of tetrahydrofuran is added. The reaction medium is stirred at room temperature for 12 hours. Saturated ammonium chloride solution is added and the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a 7/3 heptane/ethyl acetate mixture. 1.6 g (84%) of ethyl (E)-3-(4-iodo-3-propoxyphenyl)-2-methylacrylate are obtained.

Workup

customprecooled to 0° C
stirringThe reaction medium is stirred at room temperature for 12 hours
extractionthe reaction medium is extracted with ethyl acetate
dry with materialThe organic phase is dried over magnesium sulfate
filtrationfiltered
customevaporated
customThe residue obtained
customis purified by chromatography on a column of silica
washeluted with a 7/3 heptane/ethyl acetate mixture

Sources & evidence

ORD record: ord-fbc496293daa45299d29a1af7b3d3e37
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383652B2

Reaction notes

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