Trimethyl orthoformate → HCID 86605481, compound

HRID 2103025Notes

Reaction equation

HRID 2103025 reaction equation
[SH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.C(OC)(OC)OC.[CH2:18]([O:20][C:21](=[O:27])[CH:22]=[C:23]1[CH2:26][CH2:25][CH2:24]1)C>CO.S(=O)(=O)(O)O>[OH:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([S:1][C:23]2([CH2:22][C:21]([O:20][CH3:18])=[O:27])[CH2:26][CH2:25][CH2:24]2)=[CH:3][C:4]=1[CH3:10]

Participants

6

Reactant 3

HCID 9005Trimethyl orthoformateHCID 148465Phenol, 4-mercapto-2,6-dimethyl-HCID 15724666Cyclobutylidene-acetic acid ethyl ester

Product 1

HCID 86605481HCID 86605481, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-mercapto-2,6-dimethylphenol (2.5 g) in anhydrous methanol (40 mL) containing trimethyl orthoformate (3 mL), was added cyclobutylidene-acetic acid ethyl ester (7.6 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 saturated NaHCO3 and extracted with ethyl acetate. After concentrated in vacuo, the residue was purified by flash chromatography eluted with 10-20% ethyl acetate in hexane to give 3.1 g of methyl {1-[(4-hydroxy-3,5-dimethylphenyl)thio]cyclobutyl}acetate 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 saturated NaHCO3
  6. extractionextracted with ethyl acetate
  7. concentrationAfter concentrated in vacuo
  8. customthe residue was purified by flash chromatography
  9. washeluted with 10-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b89255f67e714d1db2ffa532d3e2cdcc
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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