Dimethylacetylene → Dimethyl 2,3-dimethyl-2-cyclopropene-1,1-dicarboxylate

HRID 487030

Reaction equation

HRID 487030 reaction equation
[CH3:1][C:2]#[C:3][CH3:4].[N+](=[C:7]([C:12]([O:14][CH3:15])=[O:13])[C:8]([O:10][CH3:11])=[O:9])=[N-]>FC1C(F)=C(F)C(F)=C(F)C=1F.[Hg]>[CH3:1][C:2]1[C:7]([C:12]([O:14][CH3:15])=[O:13])([C:8]([O:10][CH3:11])=[O:9])[C:3]=1[CH3:4]

Participants

5

Reactant 2

HCID 10419DimethylacetyleneHCID 5476732-Diazonio-1,3-dimethoxy-3-oxoprop-1-en-1-olate

Product 1

HCID 19096835Dimethyl 2,3-dimethyl-2-cyclopropene-1,1-dicarboxylateYield 46.2%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 9805HexafluorobenzeneSolvent

Procedure

A nitrogen-degassed solution of 33.5 grams (0.69 mole) of 2-butyne and 20.0 grams (0.13 mole) of dimethyl diazomalonate in approximately 325 grams of hexafluorobenzene was photolyzed for approximately 100 hours, at 0° C.-5° C., employing a 100-watt Hanovia mercury lamp in a manner similar to that described in Example XCVI Part A. Similar workup of the reaction mixture afforded 10.8 grams (0.06 mole) of dimethyl 2,3-dimethyl-2-cyclopropene-1,1-dicarboxylate. NMR analysis of the product indicated the following:

Sources & evidence

ORD record
ord-7456c4302f8c4d1c820cddec652ef071
Source dataset
uspto-grants-1994_03
Patent number
US05292937

Linked notes

Loading…