Sulfuric acid magnesium salt (1:1) → HCID 86739678, compound

HRID 1632474Notes

Reaction equation

[CH3:1]/[C:2](/[CH:9]=[CH:10]/[CH:11]=[C:12](\[CH3:29])/[CH:13]=[CH:14]/[C:15]1[C:20]([CH3:21])=[CH:19][C:18]([O:22][C:23]([F:26])([F:25])[F:24])=[C:17]([CH3:27])[C:16]=1[CH3:28])=[CH:3]\[C:4](OCC)=[O:5].[H-].C([Al+]CC(C)C)C(C)C.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl.CCCCCC>[CH3:1]/[C:2](=[CH:9]\[CH:10]=[CH:11]\[C:12](\[CH3:29])=[CH:13]\[CH2:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([O:22][C:23]([F:24])([F:26])[F:25])=[C:17]([CH3:27])[C:16]=1[CH3:28])/[CH:3]=[CH:4]/[OH:5]

Participants

Conditions

Temperature: -10 °C

Procedure

Ethyl (2E,4E,6E,8E)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(trifluoromethoxy)phenyl]-nonatetraenoate could be dissolved in methylene chloride and treated with diisobutylaluminum hydride in hexane solution at -60° C. under argon. The temperature is raised to -10° C. for 10 to 30 minutes and then a saturated solution of magnesium sulfate is added. The mixture is stirred at 25° C. for 2 hours, filtered and evaporated to give (2E,4E,6E,8E)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(trifluoromethoxy)phenyl]-nonatetraen-1-ol which is further purified by conventional chromatography.

Workup

filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-8ce1528f070a4082a44a006972df7d83
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04476056

Reaction notes

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