Ethanol → HCID 22934880, compound

HRID 254209Notes

Reaction equation

HRID 254209 reaction equation
[CH2:1](O)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:23][CH2:24][C:25]1([CH3:44])[O:29][N:28]=[C:27]([S:30][CH2:31][C:32]2[C:33]([C:40]([F:43])([F:42])[F:41])=[N:34][N:35]([CH2:38][CH3:39])[C:36]=2[OH:37])[CH2:26]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.C(OCC)(=O)C.O>[Cl:23][CH2:24][C:25]1([CH3:44])[O:29][N:28]=[C:27]([S:30][CH2:31][C:32]2[C:33]([C:40]([F:43])([F:42])[F:41])=[N:34][N:35]([CH2:38][CH3:39])[C:36]=2[O:37][CH2:1][CH3:2])[CH2:26]1

Participants

8

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178463143HCID 178463143, compound

Product 1

HCID 22934880HCID 22934880, compoundYield 86.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.3 g (5.4 mmoles) of ethanol and 1.4 g (5.4 mmoles) of triphenylphosphine were added, at room temperature, into a solution of 1.6 g (4.5 mmoles) of 5-chloromethyl-3-(1-ethyl-5-hydroxy-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5-meth-yl-2-isoxazoline dissolved in 20 ml of tetrahydrofuran. Thereto was added, with ice-cooling, 1.1 g (5.4 mmoles) of diisopropyl azodicarboxylate. The mixture was stirred for 1 hour to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water and extraction with ethyl acetate was conducted. The resulting organic layer was washed with water and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to reduced pressure distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography to obtain 1.5 g (yield: 86.8%) of 5-chloromethyl-3-(5-ethoxy-1-ethyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5-methyl-2-isoxazoline.

Workup

  1. additionThereto was added, with ice-
  2. temperaturecooling
  3. customto give rise
  4. customto a reaction
  5. customAfter the completion of the reaction
  6. washThe resulting organic layer was washed with water
  7. dry with materialan aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
  8. distillationThe resulting solution was subjected to reduced pressure distillation
  9. customto remove the solvent
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f5f48230c3334482a66c831d6472c8f1
Source dataset
uspto-grants-2011_01
Patent number
US07875606B2

Reaction notes

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