Hydrochloric Acid → HCID 14989148, compound

HRID 484170Notes

Reaction equation

HRID 484170 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])[CH3:3].C(N(CC)CC)C.[CH3:24][C:25]([CH:27]=[CH2:28])=[O:26].Cl>CO>[CH3:4][C:2]([C:5]1[CH:10]=[C:9]([S:11][CH2:28][CH2:27][C:25](=[O:26])[CH3:24])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6570Methyl vinyl ketoneHCID 8471TriethylamineHCID 703702,6-Di-tert-butyl-4-mercaptophenol

Product 1

HCID 14989148HCID 14989148, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound of Example 2 (2.0 g) was dissolved in methanol (20 ml) and triethylamine (0.5 ml) added followed by methylvinylketone (0.0084 mole). The reaction was stirred under nitrogen for about 20 hours. 0.1N Hydrochloric acid (80 ml) was added and the aqueous phase extracted with ethyl ether. The organic extracts were dried over sodium sulfate, filtered, the solvent removed in vacuo and the residue chromatographed on silica to give the title compound, m.p. ca. 79°-81° C.

Workup

  1. extractionthe aqueous phase extracted with ethyl ether
  2. dry with materialThe organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customthe residue chromatographed on silica

Sources & evidence

ORD record
ord-25dffc17aafe4db5b7fd171e0499bb16
Source dataset
uspto-grants-1993_07
Patent number
US05229421

Reaction notes

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