Ethyl Bromide → HCID 15432604, compound

HRID 618089Notes

Reaction equation

HRID 618089 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)=[O:13])=[CH:2]1.[CH2:26](Br)[CH3:27].[H-].[Na+]>CN(C)C=O.O1CCCC1>[CH2:26]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)=[O:13])=[CH:2]1)[CH3:27]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 9927763170488-48-9

Product 1

HCID 15432604HCID 15432604, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 1 (1.69 g) obtained in Example 1 was dissolved in a mixed solvent of N,N-dimethylformamide (12.5 ml) and tetrahydrofuran (12.5 ml), and ethyl bromide (817.3 mg) and sodium hydride (300 mg, 60% mineral oil dispersion) were added thereto, followed by stirring at room temperature for 3 hours. Ice was added to the reaction solution, and the mixture was subjected to partitioning between ethyl acetate and water. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure, and the residue was recrystallized from 2-propanol to give Compound 3 (1.54 g).

Workup

  1. additionwere added
  2. additionIce was added to the reaction solution
  3. customto partitioning between ethyl acetate and water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-576cf53ba1c04381a145ce5e02db2cf3
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Reaction notes

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