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

HRID 443367Notes

Reaction equation

HRID 443367 reaction equation
O1CCCCC1[O:7][CH2:8][CH:9]=[C:10]([CH3:28])[CH2:11][CH2:12][CH:13]=[C:14]([CH:26]=[O:27])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:25])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23].C(=O)([O-])O.[Na+].[BH4-].[Na+].C([O-])(=O)C>CO.C(O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[OH:27][CH2:26]/[C:14](/[CH2:15][CH2:16]/[CH:17]=[C:18](\[CH3:25])/[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:13]/[CH2:12][CH2:11]/[C:10](/[CH3:28])=[CH:9]/[CH2:8][OH:7]

Participants

9

Reactant 4

HCID 175AcetateHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 569911137-Formyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol tetrahydropyranyl ether

Product 1

HCID 6373042(2E,6E)-2-[(3E)-4,8-Dimethylnona-3,7-dien-1-YL]-6-methylocta-2,6-diene-1,8-diolYield 83.7%

Reagents, catalysts & solvents 4

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In 100 ml of methanol was dissolved 10.0 g of 7-formyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol tetrahydropyranyl ether prepared in Example 2-(1), and to this solution was added 100 mg of p-toluenesulfonic acid. The mixture was allowed to stand overnight at room temperature and neutralized with an aqueous sodium hydrogencarbonate solution. The methanol was distilled off, and the residue was extracted with ether, (E,E,E)-7-Formyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol obtained from the ethereal layer was dissolved in 60 ml of ethanol. After addition of 5.5 g of sodium borohydride under ice-cooling, the solution was vigorously stirred for 2 hours. The mixture was then treated with dilute acetate acid and, after addition of water, extracted with ether. The oil obtained from the ethereal layer was purified by the silica gel column chromatography, yielding 6.6 g of the desired (E,E,E)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol.

Workup

  1. distillationThe methanol was distilled off
  2. extractionthe residue was extracted with ether, (E,E,E)-7-Formyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol
  3. customobtained from the ethereal layer
  4. temperaturecooling
  5. extractionextracted with ether
  6. customThe oil obtained from the ethereal layer
  7. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-3036a7068f4149e1982451a5b43f819c
Source dataset
uspto-grants-1981_04
Patent number
US04260551

Reaction notes

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