Trityl chloride → 1-Benzyl-3-tritylglycerol

HRID 482188

Reaktionsgleichung

Reaktionsgleichung von HRID 482188
[CH2:1]([O:8][CH2:9][CH:10]([CH2:12][OH:13])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH:10]([CH2:12][O:13][C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6456Trityl chlorideHCID 980723-(Benzyloxy)-1,2-propanediol

Produkt 1

HCID 36083721-Benzyl-3-tritylglycerolAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

rac-1-O-Benzylglycerol (5.37 g, 29.5 mmol), trityl chloride (8.31 g, 29.8 mmol) and anhydrous pyridine (35 ml) were placed in a flame-dried 200 ml round-bottomed flask. The reaction mixture was stirred under anhydrous conditions at room temperature for two days. The precipitate which formed was filtered before H2O and ether were added. The ether layer was extracted with H2O, 1N HCl and H2O, and dried (MgSO4). The solvent was removed by reduced pressure to provide a viscous yellow oil. The crude product was purified by column chromatography (180 g silica gel; hexanes:ethyl acetate, gradient 8:1 to 3:1) to yield pure compound 12, rac-1-O-benzyl-3-O-tritylglycerol (9.00 g, 72% yield).

Aufarbeitung

  1. customThe precipitate which formed
  2. filtrationwas filtered before H2O and ether
  3. additionwere added
  4. extractionThe ether layer was extracted with H2O, 1N HCl and H2O
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed by reduced pressure
  7. customto provide a viscous yellow oil
  8. customThe crude product was purified by column chromatography (180 g silica gel; hexanes:ethyl acetate, gradient 8:1 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-f0c920e07153439cbef18857eeeb09e5
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05795561

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