HCID 67787613, compound → HCID 67787802, compound

HRID 273764Notes

Reaction equation

HRID 273764 reaction equation
[C:1]1([CH:7]2[CH:12]([OH:13])[CH2:11][CH2:10][CH2:9][CH:8]2[CH:14](C(O)=O)[C:15]([OH:17])=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(#N)C.[Cu-]=O>[C:1]1([CH:7]2[CH:12]([OH:13])[CH2:11][CH2:10][CH2:9][CH:8]2[CH2:14][C:15]([OH:17])=[O:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 67787613HCID 67787613, compound

Product 1

HCID 67787802HCID 67787802, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

A suspension of ca. 700 mg (2.52 mmole) of 2-(SR)-phenyl-3-(SR)-hydroxy-(SR)-cyclohexylmalonic acid in 55 mL of acetonitrile was degassed with nitrogen for 10 min and then 18 mg (0.13 mmole) of copper (I) oxide was added under nitrogen and the mixture was heated at reflux for 40 hr under nitrogen. The solution was cooled and concentrated in vacuo, and the residue was taken up in 50 mL of water containing 0.4 mL of 2N HCl and 45 mL of ether. The layers were separated and the aqueous layer was extracted with 2×50 mL of ether. The pooled organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on 67 g of silica eluting with 1 L of 100:3:0.1 methylene chloride:methanol: acetic acid to provide 530 mg (90%) of a light yellow oil that crystallized on standing.

Workup

  1. customwas degassed with nitrogen for 10 min
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 40 hr under nitrogen
  4. temperatureThe solution was cooled
  5. concentrationconcentrated in vacuo
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with 2×50 mL of ether
  8. dry with materialThe pooled organic extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash chromatography on 67 g of silica eluting with 1 L of 100:3:0.1 methylene chloride

Sources & evidence

ORD record
ord-13e43b1f82e449cab1d41e3730fb4773
Source dataset
uspto-grants-1995_02
Patent number
US05387595

Reaction notes

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