Diethyl Maleate → HCID 54117832, compound

HRID 464054Notes

Reaction equation

[CH3:1][CH2:2][C:3]([CH2:5][CH2:6]/[CH:7]=[C:8](/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])\[CH3:9])=[CH2:4].[C:16]([O:25][CH2:26][CH3:27])(=[O:24])/[CH:17]=[CH:18]\[C:19]([O:21][CH2:22][CH3:23])=[O:20]>>[CH2:26]([O:25][C:16]([CH:17]1[CH2:1][CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH2:4][CH:18]1[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:24])[CH3:27]

Participants

Reactant 2

HCID 5271566Diethyl Maleate

HCID 15228937beta Farnesene2×

Product 1

HCID 54117832HCID 54117832, compoundYield 75%

Conditions

Temperature: 180 °C

Procedure

The (E)-β-farnesene-containing product of Example 1 (10 g) and diethyl maleate (5.0 g) are heated together at 180° C. for two hours. The mixture is then distilled under reduced pressure to give 1,2-bis-(ethoxycarbonyl)-4-(4,8 dimethyl-3,7-nonadienyl) cyclohex-4-ene as a pale yellow oil (8.5 g, 75%); b.p. 175°-180° C./0.3τ; nD20 1.4894; M+ (m/z as % of base peak): 376 (6.6); δ(CCl4) 1.24 (t, 6H), 1.70 (m, 9H), 2.08 (m, 8H), 2.36 (m, 4H), 2.80 (m, 2H), 4.14 (q, 4H), 5.20 (m, 2H), 5.40 (br, t, 1H).

Workup

distillationThe mixture is then distilled under reduced pressure

Sources & evidence

ORD record: ord-8fb315b99e2b4dc38cf9006f07039521
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04546110

Reaction notes

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