Dimethyl Sulfoxide → HCID 21242392, compound

HRID 1761730Notes

Reaction equation

HRID 1761730 reaction equation
[CH2:1]([O:17][C:18]([CH:21]1[CH2:23][O:22]1)([CH3:20])[CH3:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH-].[K+].CS(C)=[O:28]>O>[CH2:1]([O:17][C:18]([CH3:19])([CH3:20])[CH:21]([OH:28])[CH2:23][OH:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 21242384HCID 21242384, compound

Product 1

HCID 21242392HCID 21242392, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
110 °C

Procedure

A mixture of 35 g of [1-(hexadecyloxy)-1-methylethyl]oxirane, 30.07 g of potassium hydroxide, 70 ml of water and 450 ml of dimethyl sulfoxide was stirred at 110° C. for 8 hours, then cooled, poured into water and extracted with ether. The ether extract was dried and the solvent removed. The residue was chromatographed via HPLC, eluting with hexane:ethyl acetate (4:1). The lower Rf component was the desired compound, giving 18.2 g of an oil.

Workup

  1. temperaturecooled
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. customwas dried
  5. customthe solvent removed
  6. customThe residue was chromatographed via HPLC
  7. washeluting with hexane:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-245a3c61536344e0942fe6de07c38259
Source dataset
uspto-grants-1989_05
Patent number
US04827011

Reaction notes

Loading…