HCID 10624529, compound → HCID 54203548, compound

HRID 322970Notes

Reaction equation

HRID 322970 reaction equation
[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:34]=[CH:33][S:32][CH:31]=2)=[CH:24][C:7]=1[O:8][CH:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>C1(C)C=CC=CC=1.[O-2].[O-2].[O-2].[Ni+3].[Ni+3]>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:34]=[CH:33][S:32][CH:31]=2)=[CH:24][C:7]=1[O:8][CH:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 1

HCID 10624529HCID 10624529, compound

Product 1

HCID 54203548HCID 54203548, compoundYield 15.6%

Reagents, catalysts & solvents 2

HCID 10313272Nickel oxide (Ni2O3)CatalystHCID 1140TolueneSolvent

Procedure

A solution of ethyl (RS)-4-[2-(4,5-dihydrooxazol-2-yl)-5- (3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate (900 mg) and nickel peroxide (5.04 g) in toluene (50 mL) is stirred at 100° C. for 2 hours. The reaction is left at ambient temperature for 16 hours then filtered through a pad of hyflo and the filtrate concentrated in vacuo. The residue is purified by flash chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (15:85 v/v). Fractions homogeneous in the required product are combined and evaporated to give ethyl (RS)-4-[2-(oxazol-2-yl)-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate (140 mg) and starting material (400 mg).

Workup

  1. filtrationthen filtered through a pad of hyflo
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue is purified by flash chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (15:85 v/v)
  4. customevaporated

Sources & evidence

ORD record
ord-e8918f58390a42be94d74758d0cdb284
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

Loading…