Chloromethyl Methyl Ether → HCID 58424857, compound

HRID 2409428Notes

Reaction equation

HRID 2409428 reaction equation
[Cl:1][C:2]1[N:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=1)=[O:5].[H-].[Na+].[CH3:26][O:27][CH2:28]Cl>CN(C)C=O>[Cl:1][C:2]1[N:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([N:6]([C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:12]=1)[CH2:26][O:27][CH3:28])=[O:5]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 58424954HCID 58424954, compound

Product 1

HCID 58424857HCID 58424857, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (100 mg, 0.31 mmol) prepared in step 2 was dissolved in N,N-dimethylformamide (3 ml), added with sodium hydride (407 mg, 10.02 mmol) at 0° C. After stirring for 30 minutes, chloromethyl methyl ether was added dropwise and the resulting mixture was stirred for 8 hours. The mixture was poured into ice water and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated to dryness. The residue was then purified by flash column chromatography (hexane:ethyl acetate=2:1) to obtain title compound (57 mg, yield: 50%, yellow liquid).

Workup

  1. stirringthe resulting mixture was stirred for 8 hours
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was then purified by flash column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-cdf7ebc32a0b4a4fbbc804d5c84efd35
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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