5-Propylcyclohexane-1,3-dione → HCID 67435389, compound

HRID 1663395Notes

Reaction equation

HRID 1663395 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:20])[C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH:5]=O.[CH3:21]/[C:22](/[NH2:26])=[CH:23]\[C:24]#[N:25].[CH2:27]([CH:30]1[CH2:35][C:34](=[O:36])[CH2:33][C:32](=O)[CH2:31]1)[CH2:28][CH3:29]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:33]3[C:34](=[O:36])[CH2:35][CH:30]([CH2:27][CH2:28][CH3:29])[CH2:31][C:32]=3[NH:26][C:22]([CH3:21])=[C:23]2[C:24]#[N:25])[CH:7]=[C:8]([OH:20])[C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1

Participants

5

Reactant 3

HCID 27372245-Propylcyclohexane-1,3-dioneHCID 53247203-AminocrotonitrileHCID 86625161HCID 86625161, compound

Product 1

HCID 67435389HCID 67435389, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromo-5-hydroxy-4-(3-methoxy-benzyloxy)-benzaldehyde (1.43 g), 3-aminocrotonitrile (350 mg) and 5-propylcyclohexane-1,3-dione (654 mg) in ethanol (100 ml) was heated at 80° C. for 17 h. The mixture was concentrated in vacuo and then purified by chromatography on silicagel in heptane/ethyl acetate 1/0→0/1 (v/v) as eluent.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by chromatography on silicagel in heptane/ethyl acetate 1/0→0/1 (v/v) as eluent

Sources & evidence

ORD record
ord-d80bc730796646929c7ad1e75a549986
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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