2,3-Dimethyl-2-butene → Dimethyl 2,2,3,3-tetramethylcyclopropanedicarboxylate

HRID 487028

Reaction equation

HRID 487028 reaction equation
[N+](=[C:3]([C:8]([O:10][CH3:11])=[O:9])[C:4]([O:6][CH3:7])=[O:5])=[N-].[CH3:12][C:13](=[C:15]([CH3:17])[CH3:16])[CH3:14]>[Hg]>[CH3:12][C:13]1([CH3:14])[C:15]([CH3:17])([CH3:16])[C:3]1([C:8]([O:10][CH3:11])=[O:9])[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 112502,3-Dimethyl-2-buteneHCID 5476732-Diazonio-1,3-dimethoxy-3-oxoprop-1-en-1-olate

Product 1

HCID 13415962Dimethyl 2,2,3,3-tetramethylcyclopropanedicarboxylateYield 30.8%

Reagents, catalysts & solvents 1

HCID 23931MercuryCatalyst

Procedure

A mixture of 20.0 grams (0.13 mole) of dimethyl diazomalonate and 164.35 grams (1.95 moles) of 2,3-dimethyl-2-butene was photolyzed at room temperature for a period of approximately 47 hours in the presence of a 100-watt Hanovia mercury lamp. Most of the unreacted 2,3-dimethyl-2-butene was removed by distillation, at atmospheric pressure, to a head temperature of 73° C. and the still residue was subjected to flash chromatography on a silica gel column to give 9.00 grams (0.04 mole) of dimethyl 2,2,3,3-tetramethylcyclopropanedicarboxylate. NMR analysis of the product indicated the following:

Workup

  1. customMost of the unreacted 2,3-dimethyl-2-butene was removed by distillation, at atmospheric pressure, to a head temperature of 73° C.

Sources & evidence

ORD record
ord-00b6f8f1372f4d36a710da393e7c716f
Source dataset
uspto-grants-1994_03
Patent number
US05292937

Linked notes

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