Hydrochloric Acid → 3,7,11,15-Tetramethylhexadec-2-enal

HRID 2352387Notes

Reaction equation

HRID 2352387 reaction equation
Br[CH:2]=[CH:3][O:4][Si](C)(C)C.C([Li])(C)(C)C.[CH3:14][CH:15]([CH2:22][CH2:23][CH2:24][CH:25]([CH3:32])[CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:16][CH2:17][CH2:18][C:19](=O)[CH3:20].Cl>C(OCC)C.CCCCC>[CH3:20][C:19]([CH2:18][CH2:17][CH2:16][CH:15]([CH3:14])[CH2:22][CH2:23][CH2:24][CH:25]([CH3:32])[CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:2][CH:3]=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 104082-pentadecanone, 6,10,14-trimethyl-HCID 53989115[(2-Bromoethenyl)oxy](trimethyl)silaneHCID 178418306HCID 178418306, compound

Product 1

HCID 542561913,7,11,15-Tetramethylhexadec-2-enalYield 80.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8003PentaneSolvent

Conditions

Temperature
-70 °C

Procedure

1-Bromo-2-trimethylsilyloxyethylene (1 g, 5.3 mmol) in anhydrous ethyl ether (10 cc) is introduced under an argon atmosphere into a 50-cc round-bottomed flask. The mixture is cooled to -70° C. and a 1.2M solution (8 cc) of tert-butyllitium in pentane is then added. Stirring is performed for 90 minutes at -70° C. and then 6,10,14-trimethyl-2-pentadecanone (1.19 g) is added in solution in anhydrous ethyl ether (3 cc). The temperature is allowed to rise to about -15° C. and stirring is continued for 1 hour. The solution is cooled to -60° C. and 3N hydrochloric acid (7 cc) is then added over 15 minutes. Stirring is performed for 30 minutes at 10° C. After extracting with ether, washing the ether phases until neutral, drying the ether phases over magnesium sulphate, filtering and evaporating off the solvents, a product is obtained and is purified by flash chromatography. 3,7,11,15-Tetramethyl-2-hexadecenal (1.05 g) is thus obtained and is characterized by its infrared spectrum and its proton nuclear magnetic resonance spectrum.

Workup

  1. customto rise to about -15° C.
  2. stirringstirring
  3. waitis continued for 1 hour
  4. temperatureThe solution is cooled to -60° C.
  5. stirringStirring
  6. waitis performed for 30 minutes at 10° C
  7. extractionAfter extracting with ether
  8. washwashing the ether phases until neutral,
  9. dry with materialdrying the ether phases over magnesium sulphate
  10. filtrationfiltering
  11. customevaporating off the solvents
  12. customa product is obtained
  13. customis purified by flash chromatography

Sources & evidence

ORD record
ord-ce8d7618faba421985e626ce19f87d64
Source dataset
uspto-grants-1989_10
Patent number
US04876370

Reaction notes

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