Vinyl isobutyl ether → HCID 86759419, compound

HRID 2085628Notes

Reaction equation

HRID 2085628 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[OH:18][CH2:19][C@H:20]([CH3:25])[C:21]([O:23][CH3:24])=[O:22].[CH:26]([O:28][CH2:29][CH:30]([CH3:32])[CH3:31])=[CH2:27]>C1(C)C=CC=CC=1>[CH3:25][C@@H:20]([CH2:19][O:18][CH:26]([O:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH3:27])[C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 7992Vinyl isobutyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10192563methyl (2S)-3-hydroxy-2-methylpropanoate

Product 1

HCID 86759419HCID 86759419, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A catalytic amount of pyridinium para-toluenesulfonate was added to 5.9 g (0.05 mole) of methyl (S)-(+)-3-hydroxy-2-methylpropionate. Thereto was dropwise added 5.5 g (0.055 mole) of isobutyl vinyl ether at room temperature. Then, stirring was conducted at room temperature for 4 hours to give rise to a reaction. Thereto was added 100 ml of toluene. The resulting mixture was washed with 50 ml of a 0.1% aqueous sodium hydroxide solution and 20 ml of water in this order. The washed material was subjected to vacuum distillation to remove the solvent, whereby was obtained 10.5 g (yield: 97.0.%) of an oily title compound (diastereomixture).

Workup

  1. customat room temperature
  2. customto give rise
  3. customto a reaction
  4. washThe resulting mixture was washed with 50 ml of a 0.1% aqueous sodium hydroxide solution and 20 ml of water in this order
  5. distillationThe washed material was subjected to vacuum distillation
  6. customto remove the solvent

Sources & evidence

ORD record
ord-369c58ed83bb411ebfd552e6dd47a30a
Source dataset
uspto-grants-2004_04
Patent number
US06720463B1

Reaction notes

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