3-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl- → (E)-3-[2-(2,2,3-trimethylcyclopent-3-en-yl)ethenyl]dihydro-2 (3H)-furanone

HRID 36779

Reaction equation

HRID 36779 reaction equation
[CH3:1][C:2]1([CH3:11])[C:6]([CH3:7])=[CH:5][CH2:4][CH:3]1[CH2:8][CH:9]=O.[O:12]1[CH:16]=[CH:15][CH2:14][C:13]1=[O:17]>>[CH3:1][C:2]1([CH3:11])[C:6]([CH3:7])=[CH:5][CH2:4][CH:3]1/[CH:8]=[CH:9]/[CH:14]1[CH2:15][CH2:16][O:12][C:13]1=[O:17]

Participants

3

Reactant 2

HCID 984973-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-HCID 1407652(3H)-Furanone

Product 1

HCID 19937876(E)-3-[2-(2,2,3-trimethylcyclopent-3-en-yl)ethenyl]dihydro-2 (3H)-furanoneYield 42%

Procedure

The process of Example 1 was carried out except that the aldehyde was 2-(2,2,3-trimethylcyclopent-3-en-yl) ethaldehyde and the furanone did not contain a 5-methyl group to obtain (E)-3-[2-(2,2,3-trimethylcyclopent-3-en-yl)ethenyl]dihydro-2 (3H)-furanone. 1HNMR (CDCl3) [Redistilled E isomer] δ6.80 (m, 1H), 5.24 (close spaced m, 1H), 4.40 (t, 2H), 2.93 (m, 2H), 2.45-1.77 (m, 6H), 1.62 (close spaced m, 3H), 1.04 (s, 3H), 0.85 (s, 3H). BP 1.38°-156 ° C. at 0.20 mm Hg Yield 42-57%

Sources & evidence

ORD record
ord-42707ed73f7443d688a1d0d884a6bd2e
Source dataset
uspto-grants-1995_05
Patent number
US05416224

Linked notes

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