Chloromethyl Methyl Ether → HCID 68284910, compound

HRID 571602Notes

Reaction equation

HRID 571602 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:28])[N:14]([CH3:27])[N:15]=[C:16]([OH:26])[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:2].[H-].[Na+].[CH3:31][O:32][CH2:33]Cl>CN(C=O)C>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:28])[N:14]([CH3:27])[N:15]=[C:16]([O:26][CH2:31][O:32][CH3:33])[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 178436240HCID 178436240, compound

Product 1

HCID 68284910HCID 68284910, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2,6-diethyl-4-methylphenyl)-6-hydroxy-5-benzyloxy-2-methyl-3(2H)-pyridazinone (120 mg, 0.317 mmol) in dry DMF (2 ml) was added 60% sodium hydride (20 mg, 0.50 mmol) at 5° C. under nitrogen atmosphere. The mixture was stirred for 5 minutes, and then 80% chloromethyl methyl ether (0.04 ml, 0.47 mmol) was added. After ice-bath was removed, the mixture was stirred at room temperature for further 30 minutes. The reaction solution was diluted with water, and extracted with ethyl acetate 2 times. The combined organic layer was washed with water 2 times, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 115 mg of Compound (I-7-1) as oil (yield: 85%).

Workup

  1. customAfter ice-bath was removed
  2. stirringthe mixture was stirred at room temperature for further 30 minutes
  3. additionThe reaction solution was diluted with water
  4. extractionextracted with ethyl acetate 2 times
  5. washThe combined organic layer was washed with water 2 times
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-77144543fa11429086b6973ef903aebb
Source dataset
uspto-grants-2015_05
Patent number
US09029295B2

Reaction notes

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