Acetic Acid → 5-[4-(3-Oxopropoxy)benzyl]thiazolidine-2,4-dione

HRID 1599340Notes

Reaction equation

[O:1]1CCO[CH:2]1[CH2:6][CH2:7][O:8][C:9]1[CH:22]=[CH:21][C:12]([CH2:13][CH:14]2[S:18][C:17](=[O:19])[NH:16][C:15]2=[O:20])=[CH:11][CH:10]=1.C(O)(=O)C>O>[O:1]=[CH:2][CH2:6][CH2:7][O:8][C:9]1[CH:22]=[CH:21][C:12]([CH2:13][CH:14]2[S:18][C:17](=[O:19])[NH:16][C:15]2=[O:20])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 6.30 g of 5-{4-[2-(1,3-dioxolan-2-yl)ethoxy]benzyl}thiazolidine-2,4-dione (prepared as described in Preparation 106) in 50 ml of a 4:1 mixture of acetic acid and water was stirred at 60° C. for 6 hours. At the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 2.20 g of the title compound, melting at 48°-51° C.

Workup

distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure
customThe resulting residue was purified by column chromatography through silica gel
additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record: ord-795272fde090408e9658386ed1b6b106
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739345

Reaction notes

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