2-Propoxycarbonylmethyl-4,5-dimethyl-2-oxo-1,3,2-dioxaphospholane → 2,2-Dimethyl-3-(3-propoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

HRID 1494565

Reaktionsgleichung

Reaktionsgleichung von HRID 1494565
[CH3:1][C:2]1([CH3:11])[C@@H:4]([CH:5]([OH:7])[OH:6])[C@H:3]1[C:8](O)=O.[CH2:12]([O:15][C:16]([CH2:18]P1(=O)OC(C)C(C)O1)=[O:17])[CH2:13][CH3:14]>>[CH3:11][C:2]1([CH3:1])[CH:3]([CH:8]=[CH:18][C:16](=[O:17])[O:15][CH2:12][CH2:13][CH3:14])[CH:4]1[C:5]([OH:7])=[O:6]

Komponenten

3

Edukt 2

HCID 198285872-Propoxycarbonylmethyl-4,5-dimethyl-2-oxo-1,3,2-dioxaphospholaneHCID 22817332(1R,3S)-3-(Dihydroxymethyl)-2,2-dimethylcyclopropane-1-carboxylic acid

Produkt 1

HCID 545705842,2-Dimethyl-3-(3-propoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

Versuchsvorschrift

Using the procedure of Example 6, 1.26 g of the lactone of (1R,cis) 2,2-dimethyl-3-dihydroxymethyl-cyclopropane-carboxylic acid and 3.13 g of the product of Step A were reacted to obtain after crystallization from hexane 0.89 g of (1R,cis,ΔZ) 2,2-dimethyl-3-[3-oxo-3-propoxy-1-propenyl]-cyclopropane-carboxylic acid melting at 59° C. and having a specific rotation of [α]D20 =+77°±1.5° (c=1% in chloroform).

Aufarbeitung

  1. customwere reacted
  2. customto obtain
  3. customafter crystallization from hexane 0.89 g of (1R,cis,ΔZ) 2,2-dimethyl-3-[3-oxo-3-propoxy-1-propenyl]-cyclopropane-carboxylic acid melting at 59° C.
  4. customa specific rotation of [α]D20 =+77°±1.5° (c=1% in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-9632e8698b904f91b3f051ca77a09363
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05026862

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