Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 70555358, compound

HRID 66831Notes

Reaction equation

HRID 66831 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:3]1[CH3:18].[Na].[H-].[Na+].[CH2:22]([O:24][C:25](=[O:30])[C:26](Br)([CH3:28])[CH3:27])[CH3:23]>CN(C)C=O>[CH2:22]([O:24][C:25](=[O:30])[C:26]([CH3:28])([O:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[C:3]([CH3:18])=[C:4]2[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:27])[CH3:23]

Participants

6

Reactant 4

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 24758Sodium hydrideHCID 5360545Sodium2×HCID 20529098HCID 20529098, compound

Product 1

HCID 70555358HCID 70555358, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

One gram (42 m mole) of 1,2-dimethyl-3-phenyl-1H-indole-5-ol was converted to the sodium salt in 10 of absolute dimethylformamide in the presence of 223 mg (5 m mole) of 55% sodium hydride immersion in oil, and the sodium salt was mixed at room temperature with 990 mg (5 m mole) of 2-bromo-2-methyl-propanoic acid ethylester. After a reaction time of six hours, the solvent was distilled off in vacuo and the reaction product was purified by chromatography on a silicagel column (eluant: toluene/ethyl acetate (9:1)). The evaporation residue of the combined fractions, which contained the purified ester, was treated with petroleum ether.

Workup

  1. distillationAfter a reaction time of six hours, the solvent was distilled off in vacuo
  2. customthe reaction product was purified by chromatography on a silicagel column (eluant: toluene/ethyl acetate (9:1))
  3. additionwas treated with petroleum ether

Sources & evidence

ORD record
ord-858b34288f864bce914844fe53f05b23
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Reaction notes

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