Diethyl 3-methylcyclopent-3-ene-1,1-dicarboxylate → 3-Methyl-cyclopent-3-enecarboxylic acid

HRID 1285613Notes

Reaction equation

HRID 1285613 reaction equation
C12CC(CC1)CCO2.[CH3:9][C:10]1[CH2:14][C:13](C(OCC)=O)([C:15]([O:17]CC)=[O:16])[CH2:12][CH:11]=1>>[CH3:9][C:10]1[CH2:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12][CH:11]=1

Participants

3

Reactant 2

HCID 10977178Diethyl 3-methylcyclopent-3-ene-1,1-dicarboxylateHCID 217024142-Oxabicyclo[3.2.1]octane

Product 1

HCID 125754193-Methyl-cyclopent-3-enecarboxylic acid

Procedure

When m is 1, n is 2 and p is 1, the ring system is a 2-oxabicyclo[3.2.1]octane, another subclass of this invention. For example, compound XIIp ##STR27## in which R2, R5 and R6 are methyl, can be prepared by saponification and decarboxylation of diethyl 1-methylcyclopent-1-ene-4,4-dicarboxylate, prepared by the procedure of E. E. Schweiger and G. J. O'Neill, J. Org. Chem., 30, 2082 (1965), to provide 1-methylcyclopent-1-ene-4-carboxylic acid. The resulting carboxylic acid is homologated in the manner proscribed for the compounds XIp, and subsequently treated similarly to the acid of subclass IX.

Workup

  1. customprepared by the procedure of E

Sources & evidence

ORD record
ord-9aae643824174ce992debcacda7f64d6
Source dataset
uspto-grants-1986_01
Patent number
US04567283

Reaction notes

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