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

HRID 443366

Reaction equation

HRID 443366 reaction equation
C([O:4][CH2:5][CH:6]=[C:7]([CH3:28])[CH2:8][CH2:9][CH:10]=[C:11]([C:23](OCC)=[O:24])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:22])[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])(=O)C.[H-].[Al+3].[H-].[H-].C(OCC)(=O)C>CCOCC>[OH:24][CH2:23]/[C:11](/[CH2:12][CH2:13]/[CH:14]=[C:15](\[CH3:22])/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:10]/[CH2:9][CH2:8]/[C:7](/[CH3:28])=[CH:6]/[CH2:5][OH:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21584524AluminiumhydrideHCID 53654873HCID 53654873, compound

Product 1

HCID 6373042(2E,6E)-2-[(3E)-4,8-Dimethylnona-3,7-dien-1-YL]-6-methylocta-2,6-diene-1,8-diol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The ester thus obtained was further reduced by aluminum hydride (prepared from 760 mg of lithium aluminum hydride and 880 mg of aluminum chloride) in 7 ml of ether. After completion of the reaction, ethyl acetate was added to the reaction mixture, and the precipitate was filtered off. The filtrate was evaporated to dryness, yielding 3.5 g of the desired product.

Workup

  1. additionwas added to the reaction mixture
  2. filtrationthe precipitate was filtered off
  3. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-6417daee1ff942c6842215cc7af87313
Source dataset
uspto-grants-1981_04
Patent number
US04260551

Linked notes

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