5-Propylcyclohexane-1,3-dione → HCID 67413208, compound

HRID 909386Notes

Reaction equation

HRID 909386 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:21][CH:22]([CH3:24])[CH3:23])[C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)[CH:5]=O.[CH3:25]/[C:26](/[NH2:30])=[CH:27]\[C:28]#[N:29].[CH2:31]([CH:34]1[CH2:39][C:38](=[O:40])[CH2:37][C:36](=O)[CH2:35]1)[CH2:32][CH3:33]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:37]3[C:38](=[O:40])[CH2:39][CH:34]([CH2:31][CH2:32][CH3:33])[CH2:35][C:36]=3[NH:30][C:26]([CH3:25])=[C:27]2[C:28]#[N:29])[CH:7]=[C:8]([O:21][CH:22]([CH3:24])[CH3:23])[C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 27372245-Propylcyclohexane-1,3-dioneHCID 53247203-AminocrotonitrileHCID 873888803-Bromo-5-isopropoxy-4-(4-nitro-benzyloxy)-benzaldehyde

Product 1

HCID 67413208HCID 67413208, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product of step b (1.06 g), 3-aminocrotonitrile (221 mg) and 5-propylcyclohexane-1,3-dione (415 mg) in ethanol (20 ml) was stirred at 80° C. for 17 h. The reaction mixture was concentrated in vacuo and the residue was chromatographed on silica gel in heptane/EtOAc=1/1 (v/v) as eluent. Yield: 750 mg. MS-ESI: [M+H]+=594.4/596.4

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was chromatographed on silica gel in heptane/EtOAc=1/1 (v/v) as eluent

Sources & evidence

ORD record
ord-b0d54090278f41f0b2d4d3ee9cbc9484
Source dataset
uspto-grants-2011_09
Patent number
US08017782B2

Reaction notes

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