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Acetonitrile → (2R)-1-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-ol

HRID 1501895
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1501895
[CH2:1]([O:19][CH2:20][C@H:21]([CH2:23][OH:24])[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][CH2:16][CH2:17][CH3:18].[C:25]1([C:31]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)Cl)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1COCC1.C(#N)C>C(N(CC)CC)C>[CH2:1]([O:19][CH2:20][C@H:21]([CH2:23][O:24][C:31]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[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][CH2:16][CH2:17][CH3:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 6456Trityl chlorideHCID 8028TetrahydrofuranHCID 108608761-O-octadecyl-sn-glycerol

Produkt 1

HCID 12896850(2R)-1-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-olAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471
Triethylamine
Lösungsmittel

Versuchsvorschrift

39 grams (113 mmol) of (S)-1-octadecyl-glycerol and 40 grams (137 mmol) of triphenylchloromethane were added to a mixture of 500 ml of dry THF and 130 ml of dry acetonitrile. 32 ml of dry triethylamine was added and the reaction mixture was refluxed for 17 hours. The reaction mixture was then cooled to room temperature, poured on ice (1 kilogram), transferred to a separatory funnel and extracted twice with 200 ml diethyl ether. The organic phase was washed consecutively with 200 ml water, twice with 100 ml dilute (1.5%) H2SO4, 200 ml water, 200 ml concentrated aqueous sodium bicarbonate, and again with 200 ml water. The solution was then dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue, a brown oil, was dissolved in 250 ml ethyl acetate and cooled to −20° C. overnight. The mixture was centrifuged (3,500 rotations per minute) at a temperature of −10° C. (3500 RPM), and the mother liquid was then poured off. The remaining solid was dissolved in hexane and refrigerated (5±3° C.) overnight. Filtration of the precipitate yielded 50 grams of pure (R)-1-octadecyl-3-trityl-glycerol.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 17 hours
  2. additionpoured on ice (1 kilogram)
  3. customtransferred to a separatory funnel
  4. extractionextracted twice with 200 ml diethyl ether
  5. washThe organic phase was washed consecutively with 200 ml water, twice with 100 ml
  6. additiondilute (1.5%) H2SO4, 200 ml water, 200 ml concentrated aqueous sodium bicarbonate
  7. dry with materialThe solution was then dried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. dissolutionThe residue, a brown oil, was dissolved in 250 ml ethyl acetate
  10. temperaturecooled to −20° C. overnight
  11. customat a temperature of −10° C. (3500 RPM)
  12. additionthe mother liquid was then poured off
  13. dissolutionThe remaining solid was dissolved in hexane
  14. customrefrigerated (5±3° C.) overnight
  15. filtrationFiltration of the precipitate

Quellen und Nachweise

ORD-Eintrag
ord-9292d8ce940a40c4afe6ad55ab5a1ce7
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09206206B2

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