Ethyl Acetoacetate → HCID 20191525, compound

HRID 2118943Notes

Reaction equation

[CH3:1][C:2](=[CH:4][CH:5]=[C:6]([CH3:8])[CH3:7])[CH3:3].[C:9]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:10][C:11]([CH3:13])=[O:12]>>[C:9]([C:10]1[C:2]([CH3:3])([CH3:1])[CH:4]([CH2:5][CH:6]([CH3:8])[CH3:7])[O:12][C:11]=1[CH3:13])([O:15][CH2:16][CH3:17])=[O:14]

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 12992Biisocrotyl

Product 1

HCID 20191525HCID 20191525, compound

Procedure

2,5-Dimethyl-2,4-hexadiene and ethyl acetoacetate were reacted utilizing the oxidative addition procedure to obtain 4-carbethoxy-2-(2-methyl-1-propenyl)-3,3,5-trimethyl-2,3-dihydrofuran. Manganese (III) acetate obtained by the reaction potassium permanganate (19.75 grams) and manganese (II) acetate (122.5 grams) in 250 mls acetic acid was employed for the oxidation. The 2,5-dimethyl-2,4-hexadiene (27.5 gram) and ethyl acetoacetate (32.5 grams) were reacted in the presence of 0.5 grams cupric acetate catalyst. 4Carbethoxy-2-(2-methyl-1-propenyl)-3,3,5-trimethyl-2,3-dihydrofuran was recovered (61% yield) and hydrogenated in ethanol using a supported palladium catalyst (5% Pd on carbon) to obtain 4-carbethoxy-2-(2-methylpropyl)-3,3,5-trimethyl-2,3-dihydrofuran. Essentially pure (97+%) 4-carbethoxy-2-(2-methylpropyl)-3,3,5-trimethyl-2,3-dihydrofuran (B.P. 136° C. @9.2 mm Hg; nD23° 1.4642) was obtained upon distillation of the crude product. The product had a green vegetable odor. The structure of the product ##STR23## was confirmed by infrared and nuclear magnetic resonance.

Workup

custom4Carbethoxy-2-(2-methyl-1-propenyl)-3,3,5-trimethyl-2,3-dihydrofuran was recovered (61% yield)

Sources & evidence

ORD record: ord-df964f39b238436a8cd4804fd83afac6
Source dataset: uspto-grants-1987_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04681703

Reaction notes

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