2-Isopropoxycarbonylmethyl-4,5-dimethyl-2-oxo-1,3,2-dioxaphospholane → 2,2-Dimethyl-3-[3-oxo-3-isopropoxy-1-propenyl]-cyclopropane-carboxylic acid

HRID 1494567Notes

Reaction equation

HRID 1494567 reaction equation
[CH3:1][C:2]1([CH3:11])[C@@H:4]([CH:5]([OH:7])[OH:6])[C@H:3]1[C:8](O)=O.[CH:12]([O:15][C:16]([CH2:18]P1(=O)OC(C)C(C)O1)=[O:17])([CH3:14])[CH3:13]>>[CH3:11][C:2]1([CH3:1])[CH:3]([CH:8]=[CH:18][C:16](=[O:17])[O:15][CH:12]([CH3:14])[CH3:13])[CH:4]1[C:5]([OH:7])=[O:6]

Participants

3

Reactant 2

HCID 198285902-Isopropoxycarbonylmethyl-4,5-dimethyl-2-oxo-1,3,2-dioxaphospholaneHCID 22817332(1R,3S)-3-(Dihydroxymethyl)-2,2-dimethylcyclopropane-1-carboxylic acid

Product 1

HCID 540556052,2-Dimethyl-3-[3-oxo-3-isopropoxy-1-propenyl]-cyclopropane-carboxylic acid

Procedure

Using the procedure of Example 6, 0.76 g of the lactone of (1R,cis) 2,2-dimethyl-3-dihydroxymethyl-cyclopropane-carboxylic acid and 1.9 g of 2-isopropoxycarbonylmethyl-4,5-dimethyl-2-oxo-1,3,2-dioxaphospholane were reacted to obtain 1 of (1R,cis,ΔZ) 2,2-dimethyl-3-[3-oxo-3-isopropoxy-1-propenyl]-cyclopropane-carboxylic acid melting at 100° C. and having a specific rotation of [α]D20 =+71°±2° (c=1% in chloroform) and 0.09 g of the corresponding E isomer.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-88c1d2984c8a407a967e30880922caa4
Source dataset
uspto-grants-1991_06
Patent number
US05026862

Reaction notes

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