2-Methoxypropene → HCID 54558176, compound

HRID 233625Notes

Reaction equation

HRID 233625 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][OH:3].CO[C:9]([CH3:11])=[CH2:10].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:29](=O)(O)[O-:30].[Na+]>ClCCl>[CH3:6][O:5][CH:1]([O:4][CH:9]([CH3:11])[CH3:10])[C:2]([O:30][CH3:29])=[O:3]

Participants

6

Reactant 4

HCID 83002-MethoxypropeneHCID 66774Methyl GlycolateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 54558176HCID 54558176, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of methyl glycolate (5 ml, 64.8 mmol) and 2-methoxypropene (12.5 ml, 130.5 mmol) in dry dichloromethane (15 ml) at 0° C. was added catalytic amount of pyridinium p-toluene-sulfonate (100 mg). The mixture was stirred at 0° C. for 2 hours. Saturated sodium bicarbonate solution was added and methylene chloride layer was separated, dried over anhydrous magnesium sulfate. Solvent was evaporated and the product was distilled over anhydrous potassium carbonate under reduced pressure (20 mmHg) at 62°-64° C. (yield=9.9 g, 94%), 1H NMR (300 MHz, D6 -acetone) d:1.28 (6H, s), 3.15 (3H, s), 3.67 (3H, s), 4.01 (2H, s).

Workup

  1. custommethylene chloride layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customSolvent was evaporated
  4. distillationthe product was distilled over anhydrous potassium carbonate under reduced pressure (20 mmHg) at 62°-64° C. (yield=9.9 g, 94%), 1H NMR (300 MHz, D6 -acetone) d:1.28 (6H, s), 3.15 (3H, s), 3.67 (3H, s), 4.01 (2H, s)

Sources & evidence

ORD record
ord-243f02fb21304071aba38ea3445965b2
Source dataset
uspto-grants-1997_01
Patent number
US05593970

Reaction notes

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