Triphenylphosphine → 3-{1-[2-(4-Chloro-phenyl)-thiazol-5-yl]-ethoxy}-cyclopent-2-enone

HRID 2170816Notes

Reaction equation

HRID 2170816 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH:13]([OH:15])[CH3:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[C:16]1(=O)[CH2:20][CH2:19][C:18](=[O:21])[CH2:17]1.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>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([CH:13]([O:15][C:16]3[CH2:20][CH2:19][C:18](=[O:21])[CH:17]=3)[CH3:14])=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 774661,3-CyclopentanedioneHCID 5363146Diisopropyl azodicarboxylateHCID 595624751-[2-(4-Chlorophenyl)thiazol-5-yl]ethanol

Product 1

HCID 669261813-{1-[2-(4-Chloro-phenyl)-thiazol-5-yl]-ethoxy}-cyclopent-2-enoneYield 41.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[2-(4-Chloro-phenyl)-thiazol-5-yl]-ethanol (4.1 g, 17.1 mmol) in anhydrous THF (100 ml), at 0° C. under an atmosphere of nitrogen was added cyclopentane-1,3-dione (2.18 g, 22.23 mmol), followed by triphenylphosphine (5.83 g, 22.23 mmol). Diisopropylazodicarboxylate (4.31 ml, 22.23 mmol) was then added dropwise over a period of 5 minutes and the reaction allowed to warm to room temperature and stirred for 2 hours. The crude reaction mixture was dry loaded onto silica and purified by flash chromatography to give 3-{1-[2-(4-Chloro-phenyl)-thiazol-5-yl]-ethoxy}-cyclopent-2-enone (2.29 g).

Workup

  1. customThe crude reaction mixture
  2. customwas dry
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-b034e104a8ed47bbb829138096456239
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

Loading…