Tetrahydrofuran → Ethyl 3-(2-anilinothiazol-4-yl)acrylate

HRID 2107265Notes

Reaction equation

HRID 2107265 reaction equation
[NH:1]([C:8]1[S:9][CH:10]=[C:11]([CH:13]=O)[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([O:17][C:18]([CH:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:19])[CH3:16].O1CCCC1>O>[NH:1]([C:8]1[S:9][CH:10]=[C:11]([CH:13]=[CH:20][C:18]([O:17][CH2:15][CH3:16])=[O:19])[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 150535702-Anilinothiazole-4-carbaldehyde

Product 1

HCID 54052926Ethyl 3-(2-anilinothiazol-4-yl)acrylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture comprising 3.5 g of 2-anilinothiazole-4-carbaldehyde, 6.5 g of (ethoxycarbonylmethylene)triphenylphosphorane and 35 ml of tetrahydrofuran was heated at 60 ° C. for 2 hours. The reaction mixture was poured into water and extracted with benzene. The benzene extract was dried over anhydrous sodium sulfate, and the solvent was evaporated off under reduced pressure, giving an oil. This oil was purified by silica gel column chromatography. using as eluent a 9:1 mixture of benzene and ethyl acetate, giving the desired compound as yellow crystals.

Workup

  1. extractionextracted with benzene
  2. extractionThe benzene extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated off under reduced pressure
  5. customgiving an oil
  6. customThis oil was purified by silica gel column chromatography
  7. additiona 9:1 mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-7f3200267c1946fc93d2bec920aa06e4
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

Loading…