Chloromethyl Methyl Ether → methyl 6-cyclohexyl-4-(methoxymethyl)-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 505787Notes

Reaction equation

[CH:1]1([C:7]2[C:8]3[S:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][C:9]=3[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:27][O:28][CH2:29]Cl>CN(C=O)C>[CH:1]1([C:7]2[C:8]3[S:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][C:9]=3[N:10]([CH2:27][O:28][CH3:29])[C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution (0.25 M) of methyl 6-cyclohexyl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate in DMF at 0° C. was treated with NaH (1.5 eq., 60% dispersion in mineral oil), and the suspension was stirred at 0° C. for 60 min then it was treated with chloromethyl methyl ether (5 eq.). The mixture was stirred at RT for 2 h then it was quenched with ice/water and extracted with AcOEt. The combined organic phase was washed with brine and dried. Evaporation of the solvent under reduced pressure gave a residue that was purified by flash chromatography on silica gel (1:12 acetone/toluene) to afford the title compound (92%) as an oil.

Workup

stirringThe mixture was stirred at RT for 2 h
customit was quenched with ice/water
extractionextracted with AcOEt
washThe combined organic phase was washed with brine
customdried
customEvaporation of the solvent under reduced pressure
customgave a residue that
customwas purified by flash chromatography on silica gel (1:12 acetone/toluene)

Sources & evidence

ORD record: ord-1a58df095f2040b0abf41ba8ba0a6016
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781431B2

Reaction notes

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