Water → HCID 19373372, compound

HRID 129303Notes

Reaction equation

HRID 129303 reaction equation
[CH2:1]([C:4]12[CH2:11][O:10][C:7]([CH2:12][C:13]([O-:15])=[O:14])([O:8][CH2:9]1)[O:6][CH2:5]2)[CH2:2][CH3:3].[Na+].[CH2:17](Br)[C:18]#[CH:19].O>CN(C)C=O>[CH2:1]([C:4]12[CH2:9][O:8][C:7]([CH2:12][C:13]([O:15][CH2:19][C:18]#[CH:17])=[O:14])([O:6][CH2:5]1)[O:10][CH2:11]2)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 7842Propargyl bromideHCID 23675655HCID 23675655, compound

Product 1

HCID 19373372HCID 19373372, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of sodium 2-{4-n-propyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl}acetate (1.0 g) and propargyl bromide (1.8 ml of 80% solution in toluene, supplied by Aldrich) in dry dimethylformamide (30 ml) was stirred at 20° for 24 hours. Water was added and the aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with water and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo and the residue was chromatographed on silica (pre-eluted with 1:3 dichloromethane:hexane containing 3% triethylamine) and eluting with 1:3 dichloromethane:hexane containing 3% triethylamine.

Workup

  1. extractionthe aqueous mixture was extracted with diethyl ether
  2. washThe ethereal extracts were washed with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customThe solvent was removed in vacuo
  5. customthe residue was chromatographed on silica (pre-eluted with 1:3 dichloromethane:hexane containing 3% triethylamine)
  6. washeluting with 1:3 dichloromethane

Sources & evidence

ORD record
ord-dc4538f2e68f473ba0c5a1ecfaf114ce
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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