2-Methoxypropene → HCID 57093961, compound

HRID 1290069Notes

Reaction equation

HRID 1290069 reaction equation
[CH3:1][O:2][C:3]([CH3:5])=[CH2:4].[CH3:6][C:7]1[CH:12]=[CH:11][C:10](S([O-])(=O)=O)=[CH:9][CH:8]=1.[CH:17]1[CH:22]=[CH:21][NH+:20]=[CH:19][CH:18]=1.[C:23]([O-:26])(O)=[O:24].[Na+]>ClCCl>[CH2:8]([C@@H:1]1[O:2][C:3]([CH3:5])([CH3:4])[N:20]([C:23]([O:26][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:24])[C@H:21]1[CH2:22][CH:17]1[CH2:11][CH2:10][CH2:9][CH2:19][CH2:18]1)[CH:7]=[CH2:6]

Participants

5

Reactant 3

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

Product 1

HCID 57093961HCID 57093961, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxypropene (0.64 ml) and PPTS (834 mg) were added to a solution of the compound (2.2 g) obtained in Production Example 1 in dichloromethane, and the mixture was stirred at room temperature for 1 hour. After adding powdery NaHCO3, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with diethyl ether. The organic layer was washed with water and saturated brine and dried over MgSO4. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography (eluted with AcOEt/Hex=5/95 v/v) to give 1.3 g of a colorless, oily title compound (see Table 1).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over MgSO4
  7. distillationThe solvent was distilled away under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluted with AcOEt/Hex=5/95 v/v)

Sources & evidence

ORD record
ord-e7ea46ff26cb4d289398cfc1a11a1dea
Source dataset
uspto-grants-1998_05
Patent number
US05750696

Reaction notes

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