Pyridine → 4-t-Butyldimethylsilyloxy-2-(6-acetoxyhexylthio)-2-cyclopentenone

HRID 358376Notes

Reaction equation

HRID 358376 reaction equation
[Si:1]([O:8][CH:9]1[CH2:13][C:12](=[O:14])[C:11]([S:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:23](OC(=O)C)(=[O:25])[CH3:24].N1C=CC=CC=1>CO>[Si:1]([O:8][CH:9]1[CH2:13][C:12](=[O:14])[C:11]([S:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:25])[CH3:24])=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 20448815HCID 20448815, compound

Product 1

HCID 204488144-t-Butyldimethylsilyloxy-2-(6-acetoxyhexylthio)-2-cyclopentenoneYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

700 mg (2.13 mmoles) of 4(RS)-t-butyldimethylsilyloxy-2-(6-hydroxyhexylthio)-2-cyclopentenone, 1020 mg (10 mmoles) of acetic anhydride and 1580 mg (20 mmoles) of pyridine were mixed, and stirred at room temperature for 2 hours. After the reaction, methanol was added. The solvent was removed to give 795 mg of 4-t-butyldimethylsilyloxy-2-(6-acetoxyhexylthio)-2-cyclopentenone as a nearly pure product.

Workup

  1. additionwas added
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-102cf2f0862645dcbe7eff90fd1985d5
Source dataset
uspto-grants-1984_08
Patent number
US04466980

Reaction notes

Loading…