Tosylmethyl isocyanide → HCID 66584156, compound

HRID 1629993Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

To a suspension of 12.0 g (107 mmol) of potassium tert-butoxide at 60% in oil, in 100 ml of anhydrous tetrahydrofuran, is added dropwise a mixture of 13.3 g (71.1 mmol) of methyl(E)-3-(3-cyanophenyl)acrylate (CAS 193151-10-9) and 13.9 g (71.1 mmol) of tosylmethyl isocyanide (CAS 36635-61-7) dissolved in 100 ml of tetrahydrofuran, while maintaining the temperature of the reaction medium at about 25° C. The mixture is then stirred for 2 hours at room temperature, and is then partially concentrated under reduced pressure. This solution is then poured into ice-water and the reaction product is then extracted with dichloromethane. The organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure to give a brown solid, which is triturated in chloroform to give 10.8 g of methyl 4-(3-cyanophenyl)-1H-pyrrole-3-carboxylate in the form of a beige-coloured solid after cooling, filtering off and drying.

Workup

concentrationis then partially concentrated under reduced pressure
additionThis solution is then poured into ice-water
extractionthe reaction product is then extracted with dichloromethane
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 triturated in chloroform

Sources & evidence

ORD record: ord-288cdce0cf9743a6907c2d3e8f9b60c6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791119B2

Reaction notes

Loading…