Benzyl Bromide → HCID 68299250, compound

HRID 1844670Notes

Reaction equation

HRID 1844670 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]1[C:10](=[O:22])[NH:11][CH:12]([CH2:15][CH:16]2[CH2:21][CH2:20][S:19][CH2:18][CH2:17]2)[C:13]=1[OH:14].C(=O)([O-])[O-].[K+].[K+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CC(C)=O>[CH2:29]([O:14][C:13]1[CH:12]([CH2:15][CH:16]2[CH2:17][CH2:18][S:19][CH2:20][CH2:21]2)[NH:11][C:10](=[O:22])[C:9]=1[C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[CH3:1])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 68299221HCID 68299221, compound

Product 1

HCID 68299250HCID 68299250, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-(2,5-dimethyl-phenyl)-4-hydroxy-5-(tetrahydro-thiopyran-4-ylmethyl)-1,5-dihydro-pyrrol-2-one (compound P2.5) (1.0 g, 3.15 mmol), potassium carbonate (0.87 g, 6.3 mmol) and benzyl bromide (0.81 g, 4.7 mmol) in 10 ml of acetone was refluxed for 2 h. Then, the reaction mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by chromatography on silica gel. Yield: 640 mg of 4-benzyloxy-3-(2,5-dimethyl-phenyl)-5-(tetrahydro-thiopyran-4-ylmethyl)-1,5-dihydro-pyrrol-2-one as a solid.

Workup

  1. filtrationThen, the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a29c41d2eb704c97b31a60e90c58fd6d
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

Loading…