Trimethyl orthoformate → HCID 86605474, compound

HRID 2102995Notes

Reaction equation

HRID 2102995 reaction equation
[SH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[C:3]=1[CH3:11].C(OC)(OC)OC.[CH2:19]([O:21][C:22](=[O:28])[CH:23]=[C:24]1[CH2:27][CH2:26][CH2:25]1)C>CO.S(=O)(=O)(O)O>[CH3:19][O:21][C:22](=[O:28])[CH2:23][C:24]1([S:1][C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[C:3]=2[CH3:11])[CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 9005Trimethyl orthoformateHCID 157080962,3,6-Trimethyl-4-sulfanylphenolHCID 15724666Cyclobutylidene-acetic acid ethyl ester

Product 1

HCID 86605474HCID 86605474, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

4-Mercapto-2,3,6-trimethyl-phenol (1.8 g) was dissolved in anhydrous methanol (30 mL) containing trimethyl orthoformate (2 mL). To this solution was added cyclobutylidene-acetic acid ethyl ester (4.0 g) and then 5 drops of concentrated sulfuric acid. The solution was deoxygenated by bubbling with nitrogen, and was allowed to reflux for 4 days. The mixture was concentrated, washed with NaHCO3 and extracted with ethyl acetate. After concentration in vacuo, the residue was purified by flash chromatography eluted with 10-20% ethyl acetate in hexane to give 2.26 g of [1-(4-Hydroxy-2,3,5-trimethyl-phenylsulfanyl)-cyclobutyl]-acetic acid methyl ester as a white solid.

Workup

  1. customThe solution was deoxygenated
  2. customby bubbling with nitrogen
  3. temperatureto reflux for 4 days
  4. concentrationThe mixture was concentrated
  5. washwashed with NaHCO3
  6. extractionextracted with ethyl acetate
  7. concentrationAfter concentration in vacuo
  8. customthe residue was purified by flash chromatography
  9. washeluted with 10-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-79583ee2b9ba425097f30f4a2b8906e0
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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