Diethylene Glycol → HCID 14877727, compound

HRID 478102Notes

Reaction equation

HRID 478102 reaction equation
[CH2:1]([OH:7])[CH2:2][O:3][CH2:4][CH2:5]O.[H-].[Na+].[CH:10]1([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][CH:30]([CH2:33][O:34]S(C)(=O)=O)[O:31][CH3:32])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.CCCCCC.C(OCC)(=O)C>CS(C)=O>[CH:10]1([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][CH:30]([CH2:33][O:34][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:7])[O:31][CH3:32])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 24758Sodium hydrideHCID 14877725HCID 14877725, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 14877727HCID 14877727, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
75 °C

Procedure

2.03 g (19.2 millimole) of diethylene glycol was dissolved in 10 ml of dimethylsulfoxide (DMSO), to which 0.576 g (14.4 millimole) of 60% sodium hydride was added, and the mixture was stirred at 75° C. for 1 hour. The mixture was cooled to room temperature, to which 1.93 g (4.62 millimole) of 1-O-(12-cyclohexyl)dodecyl-3-O-mesyl-2-O-methylglycerol in 5 ml of DMSO was added, and the reaction mixture was stirred at 75° C. for 1 hour. After the reaction, 20 ml of ice water and 50 ml of hexane-ethyl acetate (1:1) mixture were added to the reaction mixture, and the upper layer was separated after shaking thoroughly. The aqueous layer was extracted with 20 ml of hexane-ethyl acetate (1:1), and the organic layers were combined, washed with water and dried (MgSO4), followed by evaporation of the solvent. The residue was subjected to silica gel (60 g) column chromatography, and eluted with hexane-ethyl acetate (1:1), to give 1.0 g (49%) of the above-captioned compound as colorless oil.

Workup

  1. additionwas added
  2. additionwas added
  3. stirringthe reaction mixture was stirred at 75° C. for 1 hour
  4. additionwere added to the reaction mixture
  5. customthe upper layer was separated
  6. stirringafter shaking thoroughly
  7. extractionThe aqueous layer was extracted with 20 ml of hexane-ethyl acetate (1:1)
  8. washwashed with water
  9. dry with materialdried (MgSO4)
  10. customfollowed by evaporation of the solvent
  11. washeluted with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-5f5617ecc1ec4fe482377be67a2884b9
Source dataset
uspto-grants-1989_12
Patent number
US04889953

Reaction notes

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