Ethylene Glycol → (Z)-5-(4-ethoxybenzylidene)-3-(2-hydroxyethyl)thiazolidine-2,4-dione

HRID 517599Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:7](/[CH:8]=[C:9]2/[C:10](=[O:15])[NH:11][C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2].[CH2:18](O)[CH2:19][OH:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:7](/[CH:8]=[C:9]2/[C:10](=[O:15])[N:11]([CH2:18][CH2:19][OH:20])[C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2]

Participants

Reactant 4

HCID 174Ethylene Glycol

HCID 11776Triphenylphosphine

HCID 5363146Diisopropyl azodicarboxylate

HCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

Product 1

HCID 71697555(Z)-5-(4-ethoxybenzylidene)-3-(2-hydroxyethyl)thiazolidine-2,4-dione

Procedure

The title compound 28e was prepared from compound 2 (249 mg, 1.00 mmol), ethane-1,2-diol (111 μL, 2.00 mmol), triphenylphosphine (524 mg, 2.00 mmmol) and DIAD (394 μL, 2.00 mmol) in a manner similar to that described for 9 in 95.2% (279 mg) yield as a white solid.

Workup

customyield as a white solid

Sources & evidence

ORD record: ord-13a5e5ba41af4038b9151d64720bcf46
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115122B2

Reaction notes

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