Sodium Iodide → HCID 18367418, compound

HRID 1741409Notes

Reaction equation

HRID 1741409 reaction equation
[H-].[Na+].[C:3]1([C:9]2[N:10]=[C:11]([CH:20]3[NH:24][C:23](=[O:25])[CH2:22][CH2:21]3)[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[I-].[Na+].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33]Cl>C1COCC1>[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33][N:24]1[CH:20]([C:11]2[O:12][C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:10]=2)[CH2:21][CH2:22][C:23]1=[O:25]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 699943-Methoxybenzyl chlorideHCID 18367272HCID 18367272, compound

Product 1

HCID 18367418HCID 18367418, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of NaH (60% oil, 28 mg), 5-(4,5-diphenyloxazol-2-yl)pyrrolidin-2-one (0.15 g) and sodium iodide (catalytic amount) in THF (1 ml) was added a solution of 3-methoxybenzyl chloride (0.11 g) in THF (2 ml). After being stirred for 4 days at room temperature, the reaction mixture was partitioned between ethyl acetate and water. 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-methoxybenzyl)-5-(4,5-diphenyloxazol-2-yl)pyrrolidin-2-one (0.14 g). MS (m/z): 425 (M+ +1) NMR (CDCl3, δ): 2.32-2.96 (4H, m), 3.65 (3H, s), 4.32 (1H, d, J=14.8 Hz), 4.70 (1H, d, J=14.8 Hz), 4.78 (1H, m), 6.68-6.82 (3H, m), 7.13 (1H, t, J=7.8 Hz), 7.33-7.48 (6H, m), 7.56-7.61 (4H, m)

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  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-a40c5fdafe9549fd9762c394f70cd1de
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

Loading…