Water → 5,9,13-Pentadecatrien-2-ol, 6,10,14-trimethyl-, (5E,9E)-

HRID 2225466Notes

Reaction equation

HRID 2225466 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:25])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:9][CH2:10][CH2:11][C:12](=[O:14])[CH3:13].O.[OH-].[Na+]>C(OCC)C>[CH3:7][C:8]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:25])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:9][CH2:10][CH2:11][CH:12]([OH:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 612065,9,13-Pentadecatrien-2-one, 6,10,14-trimethyl-HCID 21226445Aluminium lithium hydride

Product 1

HCID 32761835,9,13-Pentadecatrien-2-ol, 6,10,14-trimethyl-, (5E,9E)-Yield 94.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 3 liter three-neck flask equipped with a dropping funnel, a stirrer and a condenser were added 38 g of lithium aluminum hydride and 700 ml of ethyl ether in a nitrogen gas stream and the mixture was stirred while maintaining at 0 ° C. To this solution was added dropwise 262 g (1.0 mol) of compound (6) as obtained above dissolved in 500 ml of ethyl ether within about 1 hour and the mixture was further reacted under stirring at room temperature for about 13 hours. After the completion of the reaction, 380 ml of water and 380 ml of a 15% aqueous solution of sodium hydroxide were added to the reaction mixture. The white crystals thus formed were separated by filtering through 50 g of Celite, extracted with 500 ml of ethyl ether three times and then concentrated after dehydrating with sodium sulfate anhydride. 251 g of the oily substance thus obtained was purified by silica gel column chromatography (silica gel: 1000 g, developing solvent: hexane:ethyl acetate=2:1 by volume). Thus 250 g (yield: 94.7 %) of the target 6,10,14- trimethyl-5,9,13-pentadecatrien-2-ol, compound (3), was obtained.

Workup

  1. customTo a 3 liter three-neck flask equipped with a dropping funnel, a stirrer and a condenser
  2. customas obtained
  3. customthe mixture was further reacted
  4. stirringunder stirring at room temperature for about 13 hours
  5. additionwere added to the reaction mixture
  6. customThe white crystals thus formed
  7. customwere separated
  8. filtrationby filtering through 50 g of Celite
  9. extractionextracted with 500 ml of ethyl ether three times
  10. concentrationconcentrated
  11. custom251 g of the oily substance thus obtained
  12. customwas purified by silica gel column chromatography (silica gel: 1000 g, developing solvent: hexane:ethyl acetate=2:1 by volume)

Sources & evidence

ORD record
ord-357dc72785dc4f9bb8ef863a3752d77f
Source dataset
uspto-grants-1994_09
Patent number
US05344850

Reaction notes

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