Tosylmethyl isocyanide → HCID 66584760, compound

HRID 1630023Notes

Reaction equation

CC(C)([O-])C.[K+].[F:7][C:8]1[CH:9]=[C:10](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:11]=[CH:12][CH:13]=1.S([CH2:31][N+:32]#[C-:33])(C1C=CC(C)=CC=1)(=O)=O>O1CCCC1>[F:7][C:8]1[CH:9]=[C:10]([C:14]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:31][NH:32][CH:33]=2)[CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a suspension of 38.3 g (341 mmol) of potassium tert-butoxide at 60% in oil in 500 ml of anhydrous tetrahydrofuran is added dropwise a mixture of 55.2 g (284 mmol) of ethyl(E)-3-(3-fluorophenyl)acrylate (CAS 166250-00-6) and 55.5 g (284 mmol) of tosylmethyl isocyanide (CAS 36635-61-7) dissolved in 500 ml of tetrahydrofuran, while maintaining the temperature of the reaction medium at about 25° C. The mixture is then stirred for 1 hour 30 minutes at room temperature. The mixture is then poured into saturated aqueous solution and the reaction product is extracted with ethyl acetate. The organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure, to give a brown solid, which is chromatographed on a column of silica gel, eluting with dichloromethane, to give 40.7 g of ethyl 4-(3-fluorophenyl)-1H-pyrrole-3-carboxylate, in the form of a white powder after triturating in diisopropyl ether, filtering off and drying.

Workup

additionis added dropwise
additionThe mixture is then poured into saturated aqueous solution
extractionthe reaction product is extracted with ethyl acetate
dry with materialThe organic phase is dried over sodium sulfate
customthe solvent is evaporated off under reduced pressure
customto give a brown solid, which
customis chromatographed on a column of silica gel
washeluting with dichloromethane

Sources & evidence

ORD record: ord-5c0bc25f5638410e9881ab84f9393d32
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791119B2

Reaction notes

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