Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 14402913, compound

HRID 1382870Notes

Reaction equation

HRID 1382870 reaction equation
[OH:1][CH:2]([CH2:9][CH:10]([OH:13])[CH:11]=[CH2:12])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:14]12(CS(O)(=O)=O)C(C)(C)C(C[CH2:20]1)C[C:15]2=O>ClCCl.COC(OC)(C)C>[CH:11]([CH:10]1[O:13][C:14]([CH3:20])([CH3:15])[O:1][CH:2]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:9]1)=[CH2:12]

Participants

5

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 13617280Ethyl 3,5-dihydroxyhept-6-enoate

Product 1

HCID 14402913HCID 14402913, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

The crude β,δ-dihydroxy-6-heptenoic acid, ethyl 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 flash-chromatography of the residue yielded 1.1 g of 6-ethenyl-2,2-dimethyl-1,3-dioxane-4-acetic acid, ethyl ester.

Sources & evidence

ORD record
ord-32c7ba3350b5470aa7471e0394aa4fa6
Source dataset
uspto-grants-1989_02
Patent number
US04808621

Reaction notes

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