Cyclopentadiene → HCID 12987106, compound

HRID 1728967Notes

Reaction equation

HRID 1728967 reaction equation
C(Cl)(=O)C(C)C.C(Cl)C=C.[CH3:11][CH:12]([CH3:19])[C:13](=[O:18])[CH2:14][CH2:15][CH:16]=[O:17].[CH:20]1[CH2:24][CH:23]=[CH:22][CH:21]=1.CC([O-])(C)C.[K+]>>[CH3:11][CH:12]([CH3:19])[C:13](=[O:18])[CH2:14][CH2:15][CH:16]=[O:17].[CH:12]([C:13]1[CH:22]=[CH:21][CH:20]=[C:24]2[C:14]=1[CH:15]=[CH:16][CH2:23]2)([CH3:19])[CH3:11]

Participants

7

Reactant 5

HCID 7612CyclopentadieneHCID 7850Allyl chlorideHCID 62325Isobutyryl chlorideHCID 12450211HCID 12450211, compoundHCID 23665647Potassium tert-butoxide

Product 2

HCID 12450211HCID 12450211, compoundHCID 12987106HCID 12987106, compoundYield 35%

Procedure

5-Methyl-4-oxocaproaldehyde (b1) was prepared analogously to a1 by reaction of iso-butyryl chloride and allyl chloride (see I.1.). 45.6 g (356 mmol) of b1 were reacted with cyclopentadiene and potassium tert-butylate and the mixture was worked up, analogously to instructions I.1. Column chromatography gave 19.6 g (35%) of indene b2 as a yellow oil (2 double bond isomers).

Sources & evidence

ORD record
ord-a6489ec3c86e4631967c79d5514c3316
Source dataset
uspto-grants-1994_07
Patent number
US05329033

Reaction notes

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