Water → (2E,6E)-2-[(3E)-4,8-Dimethylnona-3,7-dien-1-YL]-6-methylocta-2,6-diene-1,8-diol

HRID 443365Notes

Reaction equation

C([O:4][CH2:5][C:6](=O)[CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:17])/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])(=O)C.[OH2:19]>O1CCCC1.[OH-].[K+].C(O)C>[OH:4][CH2:5]/[C:6](/[CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:17])/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:15])[CH3:16])=[CH:7]/[CH2:8][CH2:9]/[C:10](/[CH3:17])=[CH:11]/[CH2:12][OH:19]

Participants

Conditions

Temperature: -20 °C

Procedure

In 30 ml of anhydrous tetrahydrofuran was suspended 5.4 g of (E)-4-methyl-6-acetoxy-4-hexen-1-yltriphenylphosphonium iodide, and to this suspension was added dropwise two molar equivalents of a n-butyllithium-hexane solution at -20° C. in a stream of nitrogen. The mixture was stirred at -20° C. for 2 hours, and to this was further added 2.5 g of (E)-6,10-dimethyl-2-oxo-5,9-undecadien-1-ol acetate (prepared in Referential example 2) in 10 ml of anhydrous tetrahydrofuran. The resulting mixture was again stirred at room temperature for 3 hours and, after addition of ice-water, extracted with ether, and from the extract was obtained in oil. The so obtained crude oil was dissolved in 25 ml of a 5% potassium hydroxide-ethanol solution under ice-cooling, and allowed to stand for 2 hours. This was, after addition of water, extracted with ether and treated in the usual way. The resultant was then chromatographed on silica gel to yield 0.95 g of the desired product.

Workup

additionto this suspension was added dropwise two molar equivalents of a n-butyllithium-hexane solution at -20° C. in a stream of nitrogen
stirringThe resulting mixture was again stirred at room temperature for 3 hours
extractionextracted with ether
customfrom the extract was obtained in oil
customThe so obtained crude oil
temperaturecooling
waitto stand for 2 hours
extractionextracted with ether
additiontreated in the usual way
customThe resultant was then chromatographed on silica gel

Sources & evidence

ORD record: ord-082f8946beea417f8d9f4d611fbca65c
Source dataset: uspto-grants-1981_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04260551

Reaction notes

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