HCID 21388144, compound → 6-Methyl-6-(4-methylcyclohexa-1,3-dien-1-yl)hept-1-en-3-one

HRID 1833943Notes

Reaction equation

HRID 1833943 reaction equation
[CH3:1][C:2]([C:9]1[CH2:14][CH2:13][C:12]([CH3:15])=[CH:11][CH:10]=1)([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=O.[CH:16]([Li])=[CH2:17]>>[CH3:8][C:2]([C:9]1[CH2:14][CH2:13][C:12]([CH3:15])=[CH:11][CH:10]=1)([CH3:1])[CH2:3][CH2:4][C:5](=[O:7])[CH:16]=[CH2:17]

Participants

3

Reactant 2

HCID 21388144HCID 21388144, compoundHCID 178506890HCID 178506890, compound

Product 1

HCID 213881476-Methyl-6-(4-methylcyclohexa-1,3-dien-1-yl)hept-1-en-3-one

Procedure

reacting the 4-methyl-4(4-methyl-1,3-cyclohexadien-1-yl)pentanoic acid with vinyl lithium to form the intermediate 6-methyl-6(4-methyl-1,3-cyclohexadien-1-yl)hepten-3-one which is converted via an internal Diels-Alder reaction to form the 1,7,7-trimethyltricyclo[6.2.2.03,8 ]dodec-9-en-4-one.

Sources & evidence

ORD record
ord-9302cee14a134459b2b59d14c5d4f149
Source dataset
uspto-grants-1978_01
Patent number
US04067906

Reaction notes

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