Water → HCID 19026975, compound

HRID 1032946Notes

Reaction equation

HRID 1032946 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:14])[C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:8]=[O:9].[CH3:15][O:16][CH2:17]Cl.O>CN(C=O)C>[CH3:3][N:4]([CH3:14])[C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:15][O:16][CH3:17])[CH:8]=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 190269823-(Dimethylamino)-4-hydroxybenzaldehyde

Product 1

HCID 19026975HCID 19026975, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (60% in oil, 1.90 g, 47.5 mmol) in dry DMF (60 ml) was added dropwise a solution of the compound (3) (5.98 g, 36.2 mmol) obtained above in DMF (40 ml) under nitrogen atmosphere under ice-cooling. The mixture was stirred at 0° C. for 30 minutes, and thereto was added dropwise chloromethyl methyl ether (3.6 ml, 47.4 mmol). The reaction mixture was stirred at 0° C.-room temperature for 2 hours. The reaction mixture was poured into water, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated. The concentrate was purified by column chromatography on silica gel to give the title aldehyde compound (Compound A) as yellow liquid. Yield 7.17 g (95%).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at 0° C.-room temperature for 2 hours
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe concentrate was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8080489a48d943ccbfd906e453e3c9bf
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Reaction notes

Loading…