Trityl chloride → HCID 14771650, Verbindung

HRID 1650624

Reaktionsgleichung

Reaktionsgleichung von HRID 1650624
[C:1]([O:10][CH2:11][CH:12]([CH2:14][OH:15])[OH:13])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(CC)CC)C.[C:23](Cl)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:10][CH2:11][CH:12]([CH2:14][O:15][C:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[OH:13])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Komponenten

6

Edukt 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 3033877Glyceryl 1-monooctanoate

Produkt 1

HCID 14771650HCID 14771650, VerbindungAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Octanoyl-rac-glycerol (10.00 g, 45.81 mmol) and DMAP were placed in a flame-dried round bottom flask, followed by triethylamine (13.0 ml, 93.27 mmol) and CH2Cl2 (200 ml). When the solid dissolved, trityl chloride (14.07 g, 50.47 mmol) was added and the mixture was stirred at room temperature for two days. The mixture was poured into ice water and the two phases were separated. The organic layer was washed three times with 1 N HCL and twice with water, dried over MgSO4, and evaporated. The product was purified by chromatography in two batches, (150 g silica gel each with hexanes:ethyl acetate (8:1) solvent) to yield compound 43, 1-octanoyl-3-O-trityl-rac-glycerol (9.96 g, 47% yield).

Aufarbeitung

  1. dissolutionWhen the solid dissolved
  2. customthe two phases were separated
  3. washThe organic layer was washed three times with 1 N HCL
  4. dry with materialtwice with water, dried over MgSO4
  5. customevaporated
  6. customThe product was purified by chromatography in two batches

Quellen und Nachweise

ORD-Eintrag
ord-ac86975316964447b848221340d1414d
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04925649

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