Chloromethyl Methyl Ether → HCID 86659830, compound

HRID 1515307Notes

Reaction equation

HRID 1515307 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[C:9](/[C:31]([F:34])([F:33])[F:32])=[CH:10]/[C:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[CH:19]([NH:23][C:24](=[O:30])[CH2:25][CH:26]([O:28][CH3:29])[CH3:27])[CH2:18][CH2:17]3)=[N:12][OH:13])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].[Na+].[CH3:37][O:38][CH2:39]Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4](/[C:9](/[C:31]([F:34])([F:32])[F:33])=[CH:10]/[C:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[CH:19]([NH:23][C:24](=[O:30])[CH2:25][CH:26]([O:28][CH3:29])[CH3:27])[CH2:18][CH2:17]3)=[N:12][O:13][CH2:37][O:38][CH3:39])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 86659831HCID 86659831, compound

Product 1

HCID 86659830HCID 86659830, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.5 g of N-[5-{(Z)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-1-hydroxyimino-2-butenyl}-indane-1-yl]-3-methoxybutyric acid amide was dissolved in 10 ml of tetrahydrofuran, and 0.08 g of 60% sodium hydride was added to the resulting solution under ice-cold conditions, followed by stirring for 30 minutes at room temperature. The temperature was cooled again, and 0.1 g of chloromethyl methyl ether was added to the resulting solution, followed by stirring for one night at room temperature. The reaction solution was poured into ice-water, extracted with ethyl acetate, washed with saturated brine, followed by drying with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=7/3 (volume ratio)) to obtain 0.3 g of the target compound. Yield was 54%.

Workup

  1. temperatureThe temperature was cooled again
  2. stirringby stirring for one night at room temperature
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialby drying with anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=7/3 (volume ratio))

Sources & evidence

ORD record
ord-c35aeb28824142b3868fc7415388a294
Source dataset
uspto-grants-2012_07
Patent number
US08222420B2

Reaction notes

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