Triethylamine → HCID 67787118, compound

HRID 273765Notes

Reaction equation

HRID 273765 reaction equation
[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:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[C:19]1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>CO>[C:1]1([CH:7]2[CH:12]([OH:13])[CH2:11][CH2:10][CH2:9][CH:8]2[CH2:14][C:15]([O:17][CH3:19])=[O:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 67787802HCID 67787802, compound

Product 1

HCID 67787118HCID 67787118, compoundYield 1,852.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.53 g (2.26 mmole) of 2-(SR)-phenyl-3-(SR)-hydroxy-(SR)-cyclohexylacetic acid in 35 mL of methanol was treated with 22 mg (0.11 mmole) of p-toluenesulfonic acid monohydrate and the mixture was heated at reflux for 27 hr. The mixture was cooled, treated with 0.02 mL of triethylamine and concentrated in vacuo. The residue was purified by flash chromatography on 67 g of silica eluting with 1.6 L of 8:1 hexanes:ethyl acetate to give 0.506 g (90%) of an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 27 hr
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on 67 g of silica eluting with 1.6 L of 8:1 hexanes

Sources & evidence

ORD record
ord-25968b24c91c4ba79681012546f13ec3
Source dataset
uspto-grants-1995_02
Patent number
US05387595

Reaction notes

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