Water → Diisopropyl Ether

HRID 452512Notes

Reaction equation

HRID 452512 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]([F:14])([F:13])[F:12])=[CH2:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl[C:16]1[C:24]([CH3:25])=[C:23]([N+:26]([O-:28])=[O:27])[CH:22]=[CH:21][C:17]=1[CH:18]=[N:19][OH:20].C(=O)([O-])[OH:30].[K+].O>O1CCCC1>[CH:16]([O:30][CH:9]([CH3:10])[CH3:11])([CH3:24])[CH3:17].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:11]([F:14])([F:12])[F:13])[O:20][N:19]=[C:18]([C:17]3[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[C:24]([CH3:25])[CH:16]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 516893Potassium BicarbonateHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 86667536Chloro-3-methyl-4-nitrobenzaldoxime

Product 2

HCID 7914Diisopropyl EtherHCID 231598015-(3,5-Dichlorophenyl)-3-(3-methyl-4-nitrophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a solution of 1.31 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 3 and 1.17 g of -chloro-3-methyl-4-nitrobenzaldoxime in 10 ml of tetrahydrofuran, 1.15 g of potassium hydrogen carbonate and 1.50 g of water were added, and stirred at room temperature for 18 hours. After the completion of the reaction, tetrahydrofuran was removed from the reaction mixture, 3 ml of water was added, and stirred under colloing with ice for further 30 minutes. Precipitated crystal was filtered off, washed with 5 ml of water and then 5 ml of diisopropyl ether to obtain 1.29 g of the aimed product as white crystal.

Workup

  1. customwas removed from the reaction mixture, 3 ml of water
  2. additionwas added
  3. stirringstirred
  4. waitunder colloing with ice for further 30 minutes
  5. customPrecipitated crystal
  6. filtrationwas filtered off
  7. washwashed with 5 ml of water

Sources & evidence

ORD record
ord-b1893f348bed46d68c4b793fc4e20740
Source dataset
uspto-grants-2013_07
Patent number
US08492311B2

Reaction notes

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