Sodium hydride → HCID 22322020, compound

HRID 1006471Notes

Reaction equation

HRID 1006471 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]([Cl:13])[C:5]=1[CH:6]=[O:7].[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19]Cl>CN(C)C=O>[Cl:3][C:4]1[CH:11]=[C:10]([O:12][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:9]=[C:8]([Cl:13])[C:5]=1[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 5283822,6-Dichloro-4-hydroxybenzaldehyde

Product 1

HCID 22322020HCID 22322020, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

82 mg (3.4 mmol) sodium hydride was added to an ice cooled solution of 500 mg (2.6 mmol) A1 and 342 mg (2.7 mmol) methoxyethoxymethylchloride in 5 ml dry dimethylformamide and the mixture was stirred at 60° C. for 8 hours. The solvent was distilled off and the residue was partitionated between aqueous ammonia and ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness yielding 370 mg (51%) A23, which was used without further purification.

Workup

  1. distillationThe solvent was distilled off
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated to dryness
  4. customyielding 370 mg (51%) A23, which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-136f86cb57be4da1908b2b0185889327
Source dataset
uspto-grants-2004_09
Patent number
US06790852B2

Reaction notes

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