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

HRID 46508

Reaktionsgleichung

Reaktionsgleichung von HRID 46508
[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]

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Sodium hydride (3.23 g of a 57% dispersion in mineral oil, 0.067 moles) was suspended in dimethylsulfoxide (117 ml) and heated at 70°-75° C. under a nitrogen atmosphere for about 45 minutes, until hydrogen evolution stopped. Tetrahydrofuran (88 ml) was added, and the mixture was cooled to 0°-5° C. Trimethylsulfonium iodide (13.67 g, 0.067 mol) was added in portions, followed by the rapid addition of 1,2-di-O-(n-hexadecyl)-3-O-(3-formylbenzyl)-glycerol (7.0 g, 0.0106 mol) in tetrahydrofuran (58 ml). The mixture was then stirred at room temperature for 16 hours, poured into water (200 ml), and extracted with ether (3×180 ml). The combined ether extracts were washed with water (2×100 ml) and saturated sodium chloride solution (100 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure to a pale yellow oil (7.0 g, 98% yield), which was pure enough by thin layer chromatography for further reaction, as described in Example 9.

Aufarbeitung

  1. temperaturethe mixture was cooled to 0°-5° C
  2. extractionextracted with ether (3×180 ml)
  3. washThe combined ether extracts were washed with water (2×100 ml) and saturated sodium chloride solution (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-dd9622b01fab439ebc1056a120da5336
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04173641

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