2,3-Dimethyl-1,3-butadiene → dimethyl (1R,2R)-4,5-dimethyl-4-cyclohexene-1,2-dicarboxylate

HRID 128770

Reaction equation

HRID 128770 reaction equation
[CH3:1][C:2]([C:4]([CH3:6])=[CH2:5])=[CH2:3].[C:7]([O:15][CH3:16])(=[O:14])/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11]>C1(C)C=CC=CC=1>[CH3:3][C:2]1[CH2:1][C@@H:9]([C:10]([O:12][CH3:13])=[O:11])[C@H:8]([C:7]([O:15][CH3:16])=[O:14])[CH2:5][C:4]=1[CH3:6]

Participants

4

Reactant 2

HCID 105662,3-Dimethyl-1,3-butadieneHCID 637568Dimethyl Fumarate

Product 1

HCID 2767837dimethyl (1R,2R)-4,5-dimethyl-4-cyclohexene-1,2-dicarboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,3-dimethylbutadiene (9.84 g, 0.12mol) and dimethyl fumarate (14.4 g, 0.1 mol) were stirred together in toluene (40 ml) at 50° C. for 24 hr. The solvent was removed in vacuo and the solid residue recrystallised from diethyl ether, to give the title compound in 85% yield. N.m.r: δH (90 MHz, CD3OD) 3.71 (s,6H), 2.55 (m,2H), 2.10 (m,4H), 1.74 ppm (s,6H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe solid residue recrystallised from diethyl ether

Sources & evidence

ORD record
ord-d2c6027d43214ddd941a4186cdc328a5
Source dataset
uspto-grants-1995_11
Patent number
US05464873

Linked notes

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