Triethylamine → HCID 136056433, compound

HRID 1649633Notes

Reaction equation

HRID 1649633 reaction equation
C(N(CC)CC)C.[C:8]([C:13]1[C:14](=[O:28])[CH2:15][CH2:16][CH:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:18]=1[OH:19])(=O)[CH2:9][CH2:10][CH3:11].Cl.[CH2:30]([O:33][NH2:34])[CH:31]=[CH2:32]>C(O)C>[CH2:30]([O:33][N:34]=[C:8]([C:13]1[C:14](=[O:28])[CH2:15][CH2:16][CH:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:18]=1[OH:19])[CH2:9][CH2:10][CH3:11])[CH:31]=[CH2:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 198541893-Hydroxy-4-(4-methoxyphenyl)-2-(1-oxobutyl)-2-cyclohexen-1-one

Product 1

HCID 136056433HCID 136056433, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (1.2 g) was added to a solution of 2-butyryl-3-hydroxy-4-(4-methoxyphenyl)cyclohex-2-e-n-1-one (2.9 g) and O-allylhydroxylamine hydrochloride (1.2 g) in absolute ethanol (50 ml) at ambient temperature. After stirring overnight at this temperature, the ethanol was evaporated in vacuo, water was added to the residue and the aqueous solution was extracted with methylene chloride. The organic extracts were dried over anhydrous magnesium sulphate and then evaporated in vacuo. The residue was chromatographed on a silica gel column using 10% Et2O--CH2Cl2 as eluant to give the title compound (2.3 g) as a yellow oil.

Workup

  1. customthe ethanol was evaporated in vacuo, water
  2. additionwas added to the residue
  3. extractionthe aqueous solution was extracted with methylene chloride
  4. dry with materialThe organic extracts were dried over anhydrous magnesium sulphate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-8b953e3462cd479cb7bf9f1310307946
Source dataset
uspto-grants-1990_05
Patent number
US04921524

Reaction notes

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