2-Chloroethanol → HCID 71697658, compound

HRID 517600Notes

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

Participants

Reactant 4

HCID 342-Chloroethanol

HCID 11776Triphenylphosphine

HCID 5363146Diisopropyl azodicarboxylate

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

Product 1

HCID 71697658HCID 71697658, compound

Procedure

The title compound 28f was prepared from compound 2 (249 mg, 1.00 mmol), 2-chloroethanol (100 μL, 1.50 mmol), triphenylphosphine (393 mg, 1.50 mmmol) and DIAD (295 μL, 1.50 mmol) in a manner similar to that described for 9 in 88.5% (276 mg) yield as a light-yellow solid.

Workup

customyield as a light-yellow solid

Sources & evidence

ORD record: ord-af139269a70c4e1b826f98d7bbf71078
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115122B2

Reaction notes

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