Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 73102692, compound

HRID 579973Notes

Reaction equation

HRID 579973 reaction equation
[OH:1][CH:2]([CH2:8][CH:9]([OH:12])[CH:10]=[CH2:11])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[C:13]12(CS(O)(=O)=O)C(C)(C)C(C[CH2:19]1)C[C:14]2=O>ClCCl.COC(OC)(C)C>[CH:10]([CH:9]1[O:12][C:13]([CH3:19])([CH3:14])[O:1][CH:2]([CH2:3][C:4]([O:6][CH3:7])=[O:5])[CH2:8]1)=[CH2:11]

Participants

5

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 72810023HCID 72810023, compound

Product 1

HCID 73102692HCID 73102692, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

The crude β,δ-dihydroxy-6-heptenoic acid, methyl ester from the previous step was dissolved in a mixture of 30 ml of dichloromethane and 10 ml of 2,2-dimethoxypropane. Camphorsulfonic acid (0.05 g) was added, and the mixture was stirred overnight. Concentration of the reaction mixture and flashchromatography of the residue yielded 1.1 g of 6-ethenyl-2,2-dimethyl-1,3-dioxane-4- acetic acid, methyl ester which was employed in the subsequent step without further purification.

Sources & evidence

ORD record
ord-a5252afb37ea416da2f4666db719b678
Source dataset
uspto-grants-1988_06
Patent number
US04751229

Reaction notes

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