2-(Triphenylphosphoranylidene)propionaldehyde → 2-Methyl-3-(2-(2,2,2-trichloroethoxycarbonyloxymethyl)thiazol-4-yl)propenal

HRID 348243Notes

Reaction equation

HRID 348243 reaction equation
[Cl:1][C:2]([Cl:17])([Cl:16])[CH2:3][O:4][C:5]([O:7][CH2:8][C:9]1[S:10][CH:11]=[C:12]([CH:14]=O)[N:13]=1)=[O:6].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:25]([CH3:28])[CH:26]=[O:27])C=CC=CC=1>C1C=CC=CC=1>[CH3:28][C:25](=[CH:14][C:12]1[N:13]=[C:9]([CH2:8][O:7][C:5]([O:4][CH2:3][C:2]([Cl:17])([Cl:16])[Cl:1])=[O:6])[S:10][CH:11]=1)[CH:26]=[O:27]

Participants

4

Reactant 2

HCID 42809872-(Triphenylphosphoranylidene)propionaldehydeHCID 104958262-(2,2,2-Trichloroethoxycarbonyloxymethyl)thiazole-4-carboxaldehyde

Product 1

HCID 852748312-Methyl-3-(2-(2,2,2-trichloroethoxycarbonyloxymethyl)thiazol-4-yl)propenalYield 90.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-(2,2,2-trichloroethoxycarbonyloxymethyl)thiazole-4-carboxaldehyde (21.0 g) and 2-(triphenylphosphoranylidene)propionaldehyde (20.6 g) in 300 mL of benzene is heated at reflux for 3 hours, then cooled to ambient temperature and concentrated. Purification by flash column chromatography on SiO2 (hexanes/ethyl acetate, 4:1) yields the product as a clear oil (21.0 g).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. concentrationconcentrated
  4. customPurification by flash column chromatography on SiO2 (hexanes/ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-469556e705314d36acee60b27f3c60f9
Source dataset
uspto-grants-2007_02
Patent number
US07176235B2

Reaction notes

Loading…