Trityl chloride → (S)-ethyl 3-hydroxy-4-trityloxybutanoate

HRID 1168053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1168053
[OH:1][C@H:2]([CH2:9][OH:10])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(CC)CC)C.[C:18](Cl)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[OH:1][C@H:2]([CH2:9][O:10][C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

6

Edukt 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 10855622(S)-ethyl 3,4-dihydroxybutanoate

Produkt 1

HCID 10883658(S)-ethyl 3-hydroxy-4-trityloxybutanoateAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To (S)-ethyl 3,4-dihydroxybutanoate (1.40 g, 9.45 mmol) in methylene chloride (20 ml) were added triethylamine (1.15 g, 11.36 mmol) and DMAP (17 mg, 0.139 mmol) and the solution was cooled in ice bath. Trityl chloride (2.90 g, 10.4 mol) in methylene chloride (15 ml) was dropped to the solution under stirring and then stirred at room temperature over night. The reaction mixture was washed with saturated ammonium chloride and then saturated brine, dried on magnesium sulfate, filtered and condensed in vacuo. The residue was subjected to silica gel chromatography to give (S)-ethyl 3-hydroxy-4-trityloxybutanoate (1.11 g, yield 31%).

Aufarbeitung

  1. temperaturethe solution was cooled in ice bath
  2. stirringstirred at room temperature over night
  3. washThe reaction mixture was washed with saturated ammonium chloride
  4. dry with materialsaturated brine, dried on magnesium sulfate
  5. filtrationfiltered
  6. customcondensed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-abdd119dbf614fadb375c09ec1071e2a
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06620977B1

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