Allyl bromide → HCID 57827783, compound

HRID 1842118Notes

Reaction equation

HRID 1842118 reaction equation
[H-].[Na+].[CH3:3][O:4][CH:5]([O:9][CH3:10])[CH:6]([OH:8])[CH3:7].[CH2:11](Br)[CH:12]=[CH2:13]>CN(C)C=O>[CH3:3][O:4][CH:5]([O:9][CH3:10])[CH:6]([CH3:7])[O:8][CH2:13][CH:12]=[CH2:11]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 5543781,1-Dimethoxy-2-propanol

Product 1

HCID 57827783HCID 57827783, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% sodium hydride (992 mg) was added to a solution of 1,1-dimethoxy-propan-2-ol (2.49 g) in dimethylformamide (50 mL) at 0° C., followed by stirring for 15 minutes. Allyl bromide (1.96 mL) was added at the same temperature, followed by stirring for 15 minutes. Ice was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (3.46 g).

Workup

  1. stirringby stirring for 15 minutes
  2. additionIce was added to the reaction solution
  3. extractionfollowed by extraction with ethyl acetate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e34130e083004aed858d9ae603b3285c
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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