Diethylamine → Diethylamine

HRID 1720198Notes

Reaction equation

HRID 1720198 reaction equation
C([Li])CCC.[CH2:6]([NH:8][CH2:9][CH3:10])[CH3:7].[CH3:11][C:12]1([CH2:15][CH:16]([CH3:23])[CH2:17][CH:18]([CH3:22])[CH2:19][CH2:20][CH3:21])[O:14][CH2:13]1>CCOCC.CCCCCC>[CH2:6]([NH:8][CH2:9][CH3:10])[CH3:7].[CH2:11]=[C:12]([CH2:15][CH:16]([CH3:23])[CH2:17][CH:18]([CH3:22])[CH2:19][CH2:20][CH3:21])[CH2:13][OH:14]

Participants

7

Reactant 3

HCID 8021DiethylamineHCID 15332454HCID 15332454, compoundHCID 178418339Butyllithium

Product 2

HCID 8021DiethylamineHCID 15332455HCID 15332455, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

An ice-cold solution of diethylamine (3.48 g, 4.9 ml, 47.55 mmol, dried with KBr) in 10 ml of anhydrous ether was prepared. Next, 19.1 ml of a 2.5M solution of n-butyllithium in hexane was added to the diethylamine solution with stirring under a nitrogen atmosphere. After 10 minutes, a solution of 2,4,6-trimethyl-1,2-epoxynonane (6) (3.50 g, 19.0 mmol) in 10 ml of anhydrous ether was added to the reaction mixture and this mixture was refluxed for one hour. Progress of the reaction was checked by withdrawing samples, quenching with water, and analyzing by TLC. Reaction time was determined to ensure total consumption of the epoxide. Upon completion, the reaction mixture was cooled and poured into ice water. The organic layer was separated and the aqueous layer was saturated with solid sodium chloride and extracted with ether. The combined organic layers were washed with 1N hydrochloric acid, saturated sodium hydrogen carbonate solution, water, and brine. the solution was dried over sodium sulfate and solvent was removed in vacuo. Vacuum distillation at 85° -90° C. yielded 2-methylene-4,6-dimethylnonan-1-ol (7).

Workup

  1. temperaturethis mixture was refluxed for one hour
  2. customby withdrawing samples
  3. customquenching with water
  4. customReaction time
  5. customconsumption of the epoxide
  6. temperatureUpon completion, the reaction mixture was cooled
  7. additionpoured into ice water
  8. customThe organic layer was separated
  9. extractionextracted with ether
  10. washThe combined organic layers were washed with 1N hydrochloric acid, saturated sodium hydrogen carbonate solution, water, and brine
  11. dry with materialthe solution was dried over sodium sulfate and solvent
  12. customwas removed in vacuo
  13. distillationVacuum distillation at 85° -90° C.

Sources & evidence

ORD record
ord-5d97a6e824894353aa840f20f060f1bc
Source dataset
uspto-grants-1996_04
Patent number
US05505951

Reaction notes

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