Triethylamine → HCID 178445616, compound

HRID 1982113Notes

Reaction equation

HRID 1982113 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].C(N(CC)CC)C.[Br-].C(OCC[N+]1C(C)=C(CCO)SC=1)C.[CH2:30]([C@H:34]1[CH2:39][CH2:38][C@H:37]([CH2:40][CH2:41][CH:42]=[O:43])[CH2:36][CH2:35]1)[CH2:31][CH2:32][CH3:33]>O1CCOCC1>[CH2:30]([C@H:34]1[CH2:35][CH2:36][C@H:37]([CH2:40][CH2:41][C:42](=[O:43])[CH2:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])[CH2:38][CH2:39]1)[CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl Acrylate2×HCID 13148484HCID 13148484, compoundHCID 178445615HCID 178445615, compound

Product 1

HCID 178445616HCID 178445616, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

7.5 g of ethyl acrylate are dissolved in 100 ml of dry dioxan under nitrogen gasification, treated with 6.1 g of triethylamine and 1.4 g of 3-(2-ethoxyethyl)-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide and heated to 80° C. A solution of 19.6 g of 3-(trans-4-butylcyclohexyl)propanal and 7.5 g of ethyl acrylate in 50 ml of dioxan is added dropwise within 5 hours. The mixture is stirred at 80° C. for a further 15 hours, then cooled to room temperature and freed from solvent on a rotary evaporator. The residue is taken up in 200 ml of tert.butyl methyl ether and washed successively with dilute sulphuric acid, dilute sodium hydrogen carbonate solution and water. The aqueous phases are back-extracted with 100 ml of tert.butyl methyl ether. The combined organic phases are dried over sodium sulphate and freed from solvent on a rotary evaporator. The crude product of ethyl 6-(trans-4-butylcyclohexyl)-4-oxo-caproate obtained is recrystallized from ethyl acetate.

Workup

  1. temperaturecooled to room temperature
  2. customfreed from solvent on a rotary evaporator
  3. washwashed successively with dilute sulphuric acid, dilute sodium hydrogen carbonate solution and water
  4. extractionThe aqueous phases are back-extracted with 100 ml of tert.butyl methyl ether
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. customfreed from solvent on a rotary evaporator

Sources & evidence

ORD record
ord-793811b1fd1b4ec28b775e57d4dc7df7
Source dataset
uspto-grants-1986_06
Patent number
US04595521

Reaction notes

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