Sodium hydride → Dimethyl 2-methyl-2-[4-(2-quinoxalinyloxy)phenoxy]propanedioate

HRID 64585Notes

Reaction equation

HRID 64585 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:16]=[N:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Br[C:24]([CH3:33])([C:29]([O:31][CH3:32])=[O:30])[C:25]([O:27][CH3:28])=[O:26]>>[CH3:33][C:24]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:16]=[N:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:17][CH:18]=1)([C:29]([O:31][CH3:32])=[O:30])[C:25]([O:27][CH3:28])=[O:26]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 12681741Dimethyl 2-bromo-2-methylmalonateHCID 133284994-(Quinoxalin-2-yloxy)phenolHCID 178418361HCID 178418361, compound

Product 1

HCID 20236282Dimethyl 2-methyl-2-[4-(2-quinoxalinyloxy)phenoxy]propanedioate

Conditions

Temperature
70 °C

Procedure

In a nitrogen atmosphere, add a solution of 4.8 g (0.02 mole) 2-(4-hydroxyphenoxy)quinoxaline in 30 cc dimethylfornmamide to 0.8 (0.02 mole) 57% sodium hydride. When the evolution of hydrogen ceases, add 4.8 g (0.021 mole) dimethyl 2-bromo-2-methylpropanedioate dropwise. When the addition is complete, heat at approximately 70° C. until the reaction is complete. Pour the mixture into ice-water and extract with ether. Concentration of the dry ethereal extracts yield the title compound.

Workup

  1. additionWhen the addition
  2. extractionextract with ether

Sources & evidence

ORD record
ord-71e2fb953cf449008845188c76636508
Source dataset
uspto-grants-1986_09
Patent number
US04609396

Reaction notes

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