Chloromethyl ethyl ether → HCID 54413931, compound

HRID 230093Notes

Reaction equation

HRID 230093 reaction equation
[C:1]([C:5]1[O:6][CH:7]=[C:8]([C:10](=[C:13]([C:15]2[C:16]([C:22]([F:25])([F:24])[F:23])=[N:17][N:18]([CH3:21])[C:19]=2[Cl:20])[OH:14])[C:11]#[N:12])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:28]([O:30][CH2:31]Cl)[CH3:29]>C1COCC1>[C:1]([C:5]1[O:6][CH:7]=[C:8]([C:10](=[C:13]([C:15]2[C:16]([C:22]([F:23])([F:24])[F:25])=[N:17][N:18]([CH3:21])[C:19]=2[Cl:20])[O:14][CH2:31][O:30][CH2:28][CH3:29])[C:11]#[N:12])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 57031928HCID 57031928, compound

Product 1

HCID 54413931HCID 54413931, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.6 g of 2-{2-tert-butyloxazol-4-yl}-3-(5-chloro-3-trifluoromethyl-1-methyl-pyrazol-4-yl)-3-hydroxyacrylonitrile was dissolved in 5 ml of THF, and 0.07 g of 60% sodium hydride was added thereto with cooling with ice, and then stirred for 15 minutes at room temperature. 0.17 g of ethoxymethyl chloride was added thereto and stirred for 6 days at room temperature. The reaction mixture was poured into ice water, extracted with ethyl acetate, and washed with saturated saline. The resulting product was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residual product was purified through silica gel thin-layer chromatography (ethyl acetate:n-hexane=1:4) to obtain 0.1 g of the intended compound in vitreous state.

Workup

  1. temperaturewith cooling with ice
  2. stirringstirred for 6 days at room temperature
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated saline
  5. dry with materialThe resulting product was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residual product was purified through silica gel thin-layer chromatography (ethyl acetate:n-hexane=1:4)

Sources & evidence

ORD record
ord-3b83a7dafc7f4407ba2623d0b92cd577
Source dataset
uspto-grants-2009_07
Patent number
US07566683B2

Reaction notes

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