Benzyl Bromide → HCID 13518986, compound

HRID 65266Notes

Reaction equation

HRID 65266 reaction equation
[OH-].[K+].[SH:3][CH2:4][CH:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH2:9][O:8][C:6]1=[O:7].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C.C(OCC)(=O)C>[CH2:20]([S:3][CH2:4][CH:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH2:9][O:8][C:6]1=[O:7])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 20234198alpha-Mercaptomethyl-beta-(p-nitrophenyl)-gamma-butyrolactone

Product 1

HCID 13518986HCID 13518986, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 71 mg of potassium hydroxide in 6 ml of ethanol were added 253 mg of α-mercaptomethyl-β-(p-nitrophenyl)-γ-butyrolactone and 239 mg of benzyl bromide and the resulting mixture was kept at room temperature for 4 hours. After completion of the reaction, the reaction mixture was diluted with 60 ml of ethyl acetate, washed with water and saturated saline, dried over magnesium sulfate and the solvent was distilled off. The resulting crude product was purified by a silica gel column chromatography to give 218 mg (yield 50%) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. washwashed with water and saturated saline
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe resulting crude product was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-2cafb935f8da4155af7d1e7301adc72b
Source dataset
uspto-grants-1986_09
Patent number
US04613613

Reaction notes

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