Water → Acetate

HRID 893557

Reaktionsgleichung

Reaktionsgleichung von HRID 893557
[OH:1]C[CH:3]([OH:6])[CH:4]=C.O.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>N1C=CC=CC=1>[C:3]([O-:6])(=[O:15])[CH3:4].[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O-:1])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 103383-Butene-1,2-diol

Produkt 2

HCID 175AcetateHCID 85570p-Toluenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

The racemic acetate substrate was prepared by one of two methods. The diol route began with racemic 1,2-dihydroxy-3-butene which could be prepared by reacting EpB with water under neutral conditions or with acid catalysis. The diol was treated with p-toluenesulfonyl chloride (p-TsCl) in pyridine at 4° C. to afford the desired monotosylate contaminated with about 10% of the corresponding ditosylate. The monotosylate could be selectively crystallized to afford pure monotosylate in 61% yield. Hydroxytosylate was acetylated under normal conditions (Ac20, Et3N, CH2C12) to provide the acetoxy-tosylate (the desired racemic acetate) in 93% yield. The diol route is illustrated as follows: ##STR3##

Aufarbeitung

  1. customcould be prepared

Quellen und Nachweise

ORD-Eintrag
ord-3662bb7299724c8fb768ba863230b39b
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05126267

Verknüpfte Notizen

Wird geladen…