Ethyl vinyl ether → HCID 10654857, compound

HRID 2085615Notes

Reaction equation

HRID 2085615 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:18]([O:23][CH3:24])(=[O:22])[C@@H:19]([CH3:21])[OH:20].[CH:25]([O:27][CH2:28][CH3:29])=[CH2:26]>C(OCC)(=O)C>[CH2:25]([O:27][CH:28]([O:20][C@H:19]([CH3:21])[C:18]([O:23][CH3:24])=[O:22])[CH3:29])[CH3:26]

Participants

5

Reactant 3

HCID 8023Ethyl vinyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 637514(+)-Methyl lactate

Product 1

HCID 10654857HCID 10654857, compoundYield 139%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A catalytic amount of pyridinium para-toluenesulfonate was added to 20.8 g (0.2 mole) of methyl (R)-(-+)-lactate (98.9% e.e) and 18.7 g (0.26 mole) of ethyl vinyl ether. The resulting mixture was stirred at room temperature for 6 hours. After the reaction, thereto was added 100 ml of ethyl acetate, followed by washing with 70 ml of a saturated aqueous sodium hydrogen carbonate solution, 70 ml of water and 70 ml of a saturated aqueous sodium chloride solution in this order. The washed material was dried over anhydrous sodium sulfate and then subjected to vacuum distillation to remove the solvent. The resulting concentrate was subjected to distillation to obtain 49.0 g (yield: 97.8%) of an oily title compound (diastereomixture).

Workup

  1. customAfter the reaction
  2. washby washing with 70 ml of a saturated aqueous sodium hydrogen carbonate solution, 70 ml of water and 70 ml of a saturated aqueous sodium chloride solution in this order
  3. dry with materialThe washed material was dried over anhydrous sodium sulfate
  4. distillationsubjected to vacuum distillation
  5. customto remove the solvent
  6. concentrationThe resulting concentrate
  7. distillationwas subjected to distillation

Sources & evidence

ORD record
ord-998cf1e6d55445cda5b4ef04507f45d2
Source dataset
uspto-grants-2004_04
Patent number
US06720463B1

Reaction notes

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