Ethyl vinyl ether → HCID 70292549, compound

HRID 1873096Notes

Reaction equation

HRID 1873096 reaction equation
[CH3:1][C:2]1[CH2:3][C@H:4]([OH:11])[CH2:5][C:6]([CH3:10])([CH3:9])[C:7]=1[CH3:8].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH:29]([O:31][CH2:32][CH3:33])=[CH2:30].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:29]([O:31][CH:32]([O:11][C@@H:4]1[CH2:5][C:6]([CH3:10])([CH3:9])[C:7]([CH3:8])=[C:2]([CH3:1])[CH2:3]1)[CH3:33])[CH3:30]

Participants

6

Reactant 4

HCID 8023Ethyl vinyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 57184026HCID 57184026, compound

Product 1

HCID 70292549HCID 70292549, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.8 g (5.2 mmol) of (1S)-3,4,5,5-tetramethyl-3-cyclohexen-1-ol was dissolved under N2 in 5 ml of absolute methylene chloride, the solution was cooled to 0° C. and 260 mg (1.04 mmol) of pyridinium p-toluenesulfonate, and then 0.45 mg (6.2 mmol) of ethyl vinyl ether were added. The mixture was subsequently stirred at 0° C. for 1 h and then poured into a saturated aqueous NaHCO3 solution, the mixture was extracted with methylene chloride, and the extract was dried over MgSO4 and concentrated. The residue was purified by distillation to yield 1.1 g (corresponding to 97% of theory) of the abovementioned product.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. dry with materialthe extract was dried over MgSO4
  3. concentrationconcentrated
  4. distillationThe residue was purified by distillation
  5. customto yield 1.1 g (corresponding to 97% of theory) of the abovementioned product

Sources & evidence

ORD record
ord-2541252c4d1d4fe9824903e7aa414ffd
Source dataset
uspto-grants-2000_08
Patent number
US06111125

Reaction notes

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