Dimethylformamide → HCID 57830115, compound

HRID 1095406Notes

Reaction equation

HRID 1095406 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:28]([CH3:30])[CH3:29].CN(C=O)C>O>[CH:28]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1)([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 5280378Formononetin

Product 1

HCID 57830115HCID 57830115, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Formononetin (1, 1.34 g, 5 mmol) (G. Y. Gao, et. al. Bioorg. Med. Chem. 2003, 11, 4069), K2CO3 (0.69 g, 5 mol), 2-bromopropane (1.23 g, 10 mmol) and DMF (10 mL) was refluxed with stirring for 3 hrs (TLC monitoring). The mixture was then cooled and evaporated in vacuo to give a residue which was treated with H2O (50 mL). The precipitate thus obtained was collected, purified by column chromatography (MeOH/CH2Cl2=1:100), and crystallization from EtOH to give 2 (1.46 g, 94% yield). M.p.: 245-246° C.

Workup

  1. temperaturewas refluxed
  2. temperatureThe mixture was then cooled
  3. customevaporated in vacuo
  4. customto give a residue which
  5. customThe precipitate thus obtained
  6. customwas collected
  7. custompurified by column chromatography (MeOH/CH2Cl2=1:100), and crystallization from EtOH

Sources & evidence

ORD record
ord-d9161de63daa433abb98ff5669c8db42
Source dataset
uspto-grants-2012_03
Patent number
US08138184B2

Reaction notes

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