Water → HCID 21508305, compound

HRID 1579571Notes

Reaction equation

HRID 1579571 reaction equation
[H-].[Na+].[CH3:3][C:4]1[O:5][C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[C:8]=1[OH:9].Br[C:15]([CH3:21])([CH3:20])[C:16]([O:18][CH3:19])=[O:17].O>CN(C)C=O>[CH3:3][C:4]1[O:5][C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[C:8]=1[O:9][C:15]([CH3:21])([CH3:20])[C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 90097Methyl 2-bromo-2-methylpropionateHCID 21508257HCID 21508257, compound

Product 1

HCID 21508305HCID 21508305, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 9 g of sodium hydride (50 percent in oil) in 150 ml of anhydrous dimethylformamide were added drop-by-drop and while stirring 22.2 g (0.15 mol) of 2-methyl-3-hydroxy-benzofuran, care being taken to maintain the temperature at about 30°-35°C. The reaction medium was stirred for a further 15 minutes and then 27.2 g (0.15 mol) of methyl α-bromoisobutyrate were added, the temperature being maintained at 35°-40°C. Stirring was continued for 24 hours at room temperature, the reaction mixture was poured into water and extracted several times with ether. The ethereal extracts were collected, washed with water and dried over anhydrous sodium sulphate.

Workup

  1. additionwere added drop-by-drop and
  2. temperatureto maintain the temperature at about 30°-35°C
  3. temperaturethe temperature being maintained at 35°-40°C
  4. stirringStirring
  5. waitwas continued for 24 hours at room temperature
  6. extractionextracted several times with ether
  7. customThe ethereal extracts were collected
  8. washwashed with water
  9. dry with materialdried over anhydrous sodium sulphate

Sources & evidence

ORD record
ord-a329899f93af4451805695351c04cac2
Source dataset
uspto-grants-1976_01
Patent number
US03931240

Reaction notes

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