Triethylamine → HCID 14261111, compound

HRID 1085659Notes

Reaction equation

HRID 1085659 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[CH:8]1([CH2:14][CH:15]([OH:18])[CH:16]=[CH2:17])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl.CCOCC>[CH:8]1([CH2:14][CH:15]([O:18][C:1](=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4])[CH:16]=[CH2:17])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66054Isovaleryl chlorideHCID 14261103HCID 14261103, compound

Product 1

HCID 14261111HCID 14261111, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

2.4 ml (19.5 mmol) of isovaleric acid chloride are added dropwise at 0° C. to a solution of 2 75 g (17.76 mmol) of 1-cyclohexyl-3-buten-2-ol, 3 ml (21.3 mmol) of triethylamine and 430 mg (3.5 mmol) of 4-dimethylaminopyridine in 20 ml of methylene chloride. When the addition is complete, the mixture is stirred for a further 3 hours at room temperature. After diluting with ether, the mixture is washed twice with 2N HCl, twice with saturated NaHCO3 solution and twice with brine and dried over MgSO4. After concentration by evaporation, the residue is distilled in a bulb tube at 150°/0.007 mbar.

Workup

  1. additionWhen the addition
  2. washthe mixture is washed twice with 2N HCl, twice with saturated NaHCO3 solution and twice with brine
  3. dry with materialdried over MgSO4
  4. concentrationAfter concentration
  5. customby evaporation
  6. distillationthe residue is distilled in a bulb tube at 150°/0.007 mbar

Sources & evidence

ORD record
ord-9855a848696e4c3fb810da6de2f65401
Source dataset
uspto-grants-1991_04
Patent number
US05010189

Reaction notes

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