Potassium Iodide → HCID 18367258, compound

HRID 1741421Notes

Reaction equation

HRID 1741421 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][N:6]1[CH:10]([C:11]2[O:12][C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=2)[CH2:9][CH2:8][C:7]1=[O:28].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH2:37]([O:36][C:34]([CH2:33][O:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][N:6]1[CH:10]([C:11]2[O:12][C:13]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=2)[CH2:9][CH2:8][C:7]1=[O:28])=[O:35])[CH3:38]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 18367251HCID 18367251, compound

Product 1

HCID 18367258HCID 18367258, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(3-hydroxybenzyl)-5-(4,5-diphenyloxazol-2-yl)pyrrolidin-2-one (0.13 g), ethyl bromoacetate (0.21 g), potassium carbonate (99 mg) and potassium iodide (catalytic amount) in acetonitrile (10 ml) was refluxed for 9 hours. The reaction mixture was partitioned between ethyl acetate and brine. The organic layer was washed with brine. The dried solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give 1-(3-ethoxycarbonylmethoxybenzyl)-5-(4,5-diphenyloxazol-2-yl)pyrrolidin-2-one (0.16 g). MS (m/z): 497 (M+ +1) NMR (CDCl3, δ): 1.28 (3H, t, J=7.1 Hz), 2.20-2.96 (4H, m), 4.23 (2H, q, J=7.1 Hz), 4.38 (1H, d, J=14.7 Hz), 4.43 (2H, s), 4.70 (1H, d, J=14.7 Hz), 4.76 (1H, m), 6.70-6.87 (3H, m), 7.15 (1H, t, J=7.8 Hz), 7.33-7.56 (6H, m), 7.57-7.61 (4H, m)

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and brine
  2. washThe organic layer was washed with brine
  3. customThe dried solvent was evaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-aa71b55c671e4c898b7086930f35e967
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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