TRANS 5-(t-BUTYLDIPHENYLSILYLOXYMETHYL)-2-(DIETHYLOXYPHOSPHINOYL)-1,3-OXATHIOLANE → Trans-2-(Diethyloxyphosphinoyl)-5-Hydroxymethyl-1,3-Oxathiolane

HRID 636864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636864
[Si]([O:18][CH2:19][C@@H:20]1[O:24][C@@H:23]([P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])[S:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>CO.C(Cl)(=O)C.[Cl-].[NH4+]>[CH2:28]([O:27][P:25]([O:30][CH2:31][CH3:32])([C@H:23]1[S:22][CH2:21][C@H:20]([CH2:19][OH:18])[O:24]1)=[O:26])[CH3:29]

Komponenten

5

Edukt 1

HCID 131720781TRANS 5-(t-BUTYLDIPHENYLSILYLOXYMETHYL)-2-(DIETHYLOXYPHOSPHINOYL)-1,3-OXATHIOLANE

Produkt 1

HCID 86752984Trans-2-(Diethyloxyphosphinoyl)-5-Hydroxymethyl-1,3-OxathiolaneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6367Acetyl chlorideKatalysatorHCID 25517Ammonium ChlorideKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of cis and trans-5-t-butyldimethylsilyloxymethyl-2-(diethyloxyphosphinoyl)-1,3-oxathiolane (example 25) (4.00 g, 10.8 mmol) in MeOH (30 mL) was added a few drops of acetyl chloride (200 μL) at 0° C. The mixture was stirred at 0° C. for 1 hr. and at room temperature for 18 hr. A few drops of ammonium chloride was added and the solvent was evaporated under reduced pressure. The crude material was purified by several flash chromatography with a mixture of dichloromethane and methanol (96:4) to give 382 mg of the cis isomer , 1.19 g of the trans isomer and 332 mg of the mixture in a total yield of 80% after the first purification.

Aufarbeitung

  1. waitand at room temperature for 18 hr
  2. customthe solvent was evaporated under reduced pressure
  3. customThe crude material was purified by several flash chromatography with a mixture of dichloromethane and methanol (96:4)

Quellen und Nachweise

ORD-Eintrag
ord-6987f2ce568b4971a0e54f131b9f5ce5
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194576B1

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