Triethylamine → HCID 178450312, compound

HRID 981868Notes

Reaction equation

HRID 981868 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:12])[CH2:9][CH2:10][CH3:11].[CH2:14]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:27][C:26](=[O:28])[CH:25]=[C:24]([OH:29])[CH2:23]2)=[CH:18][CH:17]=1)[CH3:15]>O1CCCC1>[C:8]([C:25]1[C:26](=[O:28])[CH2:27][CH:22]([C:19]2[CH:18]=[CH:17][C:16]([CH2:14][CH3:15])=[CH:21][CH:20]=2)[CH2:23][C:24]=1[OH:29])(=[O:12])[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 14578420HCID 14578420, compound

Product 1

HCID 178450312HCID 178450312, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

51 g (0.51 mol) of triethylamine and--with ice cooling--54 g (0.51 mol) of butyryl chloride are dripped into a solution of 110 g 0.51mol) of the 5-(4-ethylphenyl)-3-hydroxy-2-cyclohexen-1-one, obtained in accordance with the foregoing instructions, in 500 ml of tetrahydrofuran. After 8 hours at room temperature, the mixture is filtered and the precipitate is washed with tetrahydrofuran. The filtrate is concentrated, the residue is taken up in 500 ml of ethyl acetate and 6.2 g of 4-N,N-dimethylaminopyridine is added. The homogeneous solution is kept for 40 hours at room temperature, is then concentrated and the residue is taken up in 10% strength potassium hydroxide solution. The undissolved constituents are separated off, and the filtrate is acidified to pH 1. The product which precipitates out is filtered off and dried under reduced pressure.

Workup

  1. filtrationthe mixture is filtered
  2. washthe precipitate is washed with tetrahydrofuran
  3. concentrationThe filtrate is concentrated
  4. addition6.2 g of 4-N,N-dimethylaminopyridine is added
  5. waitThe homogeneous solution is kept for 40 hours at room temperature
  6. concentrationis then concentrated
  7. customThe undissolved constituents are separated off
  8. customThe product which precipitates out
  9. filtrationis filtered off
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-1d284dc652ec4accb1fca8f5cdd781c7
Source dataset
uspto-grants-1991_02
Patent number
US04994106

Reaction notes

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