Benzyl Alcohol → 2-(Pyrrol-1-yl)malonic acid dibenzyl ester

HRID 256580Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:16])[CH:5]([N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20]C=1>CCO.CCO.CCO.CCO.[Ti]>[CH2:9]([O:8][C:6](=[O:7])[CH:5]([N:11]1[CH:12]=[CH:13][CH:14]=[CH:15]1)[C:4]([O:3][CH2:1][C:2]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:18]=1)=[O:16])[C:10]1[CH:18]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 2-(pyrrol-1-yl)malonic acid diethyl ester (75.7 g) in benzyl alcohol (200 ml) was added tetraethyl titanate (3.0 g), and the resulting mixture was stirred at 110° C. for 15 hours. After removal of the benzyl alcohol under reduced pressure, the residue was chromatographed on silica gel using n-hexane/ethyl acetate (10:1) as the eluent. Fractions containing the title compound were pooled and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (102.5 g, 87.3%) as colorless crystals, mp 48.5°-49° C.

Workup

customAfter removal of the benzyl alcohol under reduced pressure
customthe residue was chromatographed on silica gel
additionFractions containing the title compound
customevaporated under reduced pressure
customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record: ord-32045007fac441dfb7bc1bce30e13674
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05258382

Reaction notes

Loading…