Sodium hydride → HCID 57791153, compound

HRID 881972Notes

Reaction equation

HRID 881972 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[H-].[Na+].Br[CH2:17][CH2:18][O:19][CH3:20]>CN(C=O)C>[CH3:13][O:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([O:1][CH2:17][CH2:18][O:19][CH3:20])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 13941268Methyl 3-hydroxy-5-methoxybenzoate

Product 1

HCID 57791153HCID 57791153, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-hydroxy-5-methoxybenzoate (Example 1, step i, 0.5 g, 2.7 mmol) in DMF (10 ml) was added NaH (0.2 g, 5.4 mmol) at 0 under a nitrogen atmosphere. After stirring for minutes, 1-bromo-2-methoxy-ethane (0.75 g, 5.4 mmol) was added and the reaction mixture was stirred at 50 for 1 hour. The solution was poured into 100 ml ice water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give methyl 3-methoxy-5-(2-methoxyethoxy)benzoate (0.5 g). The crude product was used in the next step without further purification.

Workup

  1. stirringthe reaction mixture was stirred at 50 for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea62d6d4ade545c28d87d42b177fc415
Source dataset
uspto-grants-2015_03
Patent number
US08993757B2

Reaction notes

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