Sodium hydride → 1,2-Di-O-(n-hexadecyl)-3-O-[3-(1,2-epoxyethyl)benzyl]-glycerol

HRID 444068Notes

Reaction equation

HRID 444068 reaction equation
[H-].[Na+].[H][H].[I-].[CH3:6][S+](C)C.[CH2:10]([O:26][CH2:27][CH:28]([CH2:46][O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([CH:55]=[O:56])[CH:50]=1)[O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CS(C)=O.O1CCCC1.O>[CH2:10]([O:26][CH2:27][CH:28]([CH2:46][O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([CH:55]2[O:56][CH2:6]2)[CH:50]=1)[O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 234661481,2-di-O-(n-hexadecyl)-3-O-(3-formylbenzyl)-glycerolHCID 178418361HCID 178418361, compound

Product 1

HCID 234661101,2-Di-O-(n-hexadecyl)-3-O-[3-(1,2-epoxyethyl)benzyl]-glycerolYield 98%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of sodium hydride (3.23 g. of a 57 wt. % dispersion in mineral oil, 67 mmoles) in dimethylsulfoxide (117 ml.) was heated under a nitrogen atmosphere at 70° to 75° C. until hydrogen evolution stopped (45 min.). Tetrahydrofuran (88 ml.) was added and the mixture cooled to 0° to 5° C. Trimethylsulfonium iodide (13.67 g., 67 mmoles) was then added in portions, followed by rapid addition of a solution of 1,2-di-O-(n-hexadecyl)-3-O-(3-formylbenzyl)-glycerol (7.0 g., 10.6 mmoles) in tetrahydrofuran (58 ml.). The resulting mixture was stirred for 16 hours at room temperature, poured into water (200 ml.) and extracted with ether (3×180 ml.). The combined ether extract was washed with water (2×100 ml.) and saturated aqueous sodium chloride solution (100 ml.), dried (MgSO4), filtered and evaporated in vacuo to an oil (7.0 g., 98% yield), which was sufficiently pure to be used in the next step.

Workup

  1. custom(45 min.)
  2. temperaturethe mixture cooled to 0° to 5° C
  3. extractionextracted with ether (3×180 ml.)
  4. extractionThe combined ether extract
  5. washwas washed with water (2×100 ml.) and saturated aqueous sodium chloride solution (100 ml.)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo to an oil (7.0 g., 98% yield), which

Sources & evidence

ORD record
ord-7180a49e3592487386af44fb8ea008a9
Source dataset
uspto-grants-1981_04
Patent number
US04262021

Reaction notes

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