Triphenylphosphine → 3-[5-(4-Chloro-phenyl)-thiophen-2-ylmethoxy]-cyclopent-2-enone

HRID 2170822Notes

Reaction equation

HRID 2170822 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH2:13][OH:14])=[CH:11]N=2)=[CH:4][CH:3]=1.[C:15]1(=O)[CH2:19][CH2:18][C:17](=[O:20])[CH2:16]1.[C:22]1(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:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH2:13][O:14][C:15]3[CH2:19][CH2:18][C:17](=[O:20])[CH:16]=3)=[CH:11][CH:22]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 774661,3-CyclopentanedioneHCID 5363146Diisopropyl azodicarboxylateHCID 59562416[2-(4-Chlorophenyl)thiazol-5-yl]methanol

Product 1

HCID 669260683-[5-(4-Chloro-phenyl)-thiophen-2-ylmethoxy]-cyclopent-2-enoneYield 76.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [2-(4-Chloro-phenyl)-thiazol-5-yl]-methanol (4.89 g, 21.75 mmol) in anhydrous THF (100 ml), at 0° C. under an atmosphere of nitrogen was added cyclopentane-1,3-dione (2.78 g, 28.27 mmol) followed by triphenylphosphine (7.41 g, 28.27 mmol). Diisopropylazodicarboxylate (5.48 ml, 28.27 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-[5-(4-Chloro-phenyl)-thiophen-2-ylmethoxy]-cyclopent-2-enone (5.1 g).

Workup

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

Sources & evidence

ORD record
ord-e8b25da16b7541b3a0248c72ae71e5f9
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

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