Trifluoroacetic acid → HCID 19000184, compound

HRID 2260175Notes

Reaction equation

HRID 2260175 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16](=[O:31])[CH2:17][C:18]([S:21]CC2C=CC(OC)=CC=2)([CH3:20])[CH3:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[C:12]([C:9]1[CH:8]=[C:7]([C:16](=[O:31])[CH2:17][C:18]([SH:21])([CH3:20])[CH3:19])[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19000190HCID 19000190, compound

Product 1

HCID 19000184HCID 19000184, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred, ice-cold solution of 1-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-(4-methoxyphenylmethylthio)-3-methyl-butan-1-one (70 mg) in CHCl3 (1 mL), under argon, is added CF3COOH (0.02 mL) via syringe. The reaction mixture is kept at 0° C. for 3 hours, and then solvent is evaporated under reduced pressure to give a brown oil. The crude material is purified twice by preparative silica gel thin layer chromatography (hexane:ethyl acetate, 9:1), to give 1-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-sulfhydryl-3-methyl-butan-1-one as a colorless oil.

Workup

  1. customsolvent is evaporated under reduced pressure
  2. customto give a brown oil
  3. customThe crude material is purified twice by preparative silica gel thin layer chromatography (hexane:ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-d0ff6eada90e46e79ab5eb407d1c3030
Source dataset
uspto-grants-1995_12
Patent number
US05476876

Reaction notes

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