Triethylamine → HCID 87429621, compound

HRID 511748Notes

Reaction equation

HRID 511748 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[CH:12]1[C:19](=[O:20])[CH:18]2[CH:14]([CH2:15][CH:16]([CH2:21][CH2:22][CH2:23][CH:24]=O)[CH2:17]2)[C:13]1=[O:26])[CH3:2].Cl.[CH3:28][O:29][NH2:30].C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[CH2:10]([C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[CH:12]1[C:13](=[O:26])[CH:14]2[CH:18]([CH2:17][CH:16]([CH2:21][CH2:22][C:23](=[N:30][O:29][CH3:28])[CH3:24])[CH2:15]2)[C:19]1=[O:20])[CH3:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 131733270HCID 131733270, compound

Product 1

HCID 87429621HCID 87429621, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

267 mg (0.82 mmol) of 2-(2,6-diethyl-4-methylphenyl)-5-(oxobutyl)-tetrahydropentalene-1,3-dione (example I-a-39), 102 mg (1.23 mmol) of O-methylhydroxylamine hydrochloride and 0.5 ml of triethylamine in 10 ml of acetonitrile are stirred at room temperature overnight. The mixture is then taken up in ethyl acetate, washed with water and dried (magnesium sulphate) and the solvent is distilled off Chromatography on silica gel (mobile phase ethyl acetate/hexane 1:4) gives 225 mg (77%) of the target compound in the form of colourless crystals of m.p. 79-80° C.

Workup

  1. customare stirred at room temperature overnight
  2. washwashed with water
  3. dry with materialdried (magnesium sulphate)
  4. distillationthe solvent is distilled off Chromatography on silica gel (mobile phase ethyl acetate/hexane 1:4)

Sources & evidence

ORD record
ord-0063b59842c74499aa28cadf9553c964
Source dataset
uspto-grants-2015_08
Patent number
US09101133B2

Reaction notes

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