Water → HCID 86739862, compound

HRID 2412336Notes

Reaction equation

HRID 2412336 reaction equation
[O:1]([C:8]1[N:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:16]/[C:17](/[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)=[CH:18]\[C@H:19]1[C@H:21]([C:22](Cl)=[O:23])[C:20]1([CH3:26])[CH3:25].N1C=CC=CC=1.O>C1(C)C=CC=CC=1>[Cl:16]/[C:17](/[C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=1)=[CH:18]\[C@H:19]1[C@H:21]([C:22]([O:15][CH2:14][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:13]=2)=[O:23])[C:20]1([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 128791556-Phenoxy-2-pyridinemethanolHCID 44152741rel-(1R,3R)-3-[(1Z)-2-Chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarbonyl chloride

Product 1

HCID 86739862HCID 86739862, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

4.02 g (0.02 mol) of (6-phenoxy-2-pyridinyl)-methanol and 6.07 g (0.02 mol) of (±)-trans-Z-3-(2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid-chloride were dissolved in 100 ml of anhydrous toluene, and 2 g of pyridine, dissolved in 10 ml of anhydrous toluene, were added dropwise to the solution at 20°-25° C., while stirring. The mixture was then stirred for a further 3 hours at 25° C. The reaction mixture was poured into 150 ml of water, and the organic phase was separated off and again washed with 100 ml of water. The toluene phase was then dried over sodium sulphate and the solvent was distilled off in a water jet vacuum. The last solvent residues were removed by incipient distillation for a short time at a bath temperature of 60° C./1 mm Hg. 8.6 g (92% of theory) of (6-phenoxy-2-pyridinyl)-methyl (±)-trans-Z-3-(2-chloro-2-(4-chlorophenyl)-vinyl)-2,2-dimethyl-1-cyclopropanecarboxylate were obtained as a yellow viscous oil. The structure was established by the 1H-NMR spectrum.

Workup

  1. additionwere added dropwise to the solution at 20°-25° C.
  2. stirringThe mixture was then stirred for a further 3 hours at 25° C
  3. customthe organic phase was separated off
  4. washagain washed with 100 ml of water
  5. dry with materialThe toluene phase was then dried over sodium sulphate
  6. distillationthe solvent was distilled off in a water jet vacuum
  7. customThe last solvent residues were removed by incipient distillation for a short time at a bath temperature of 60° C./1 mm Hg

Sources & evidence

ORD record
ord-238c6263daaf4360a0d7502047e7d2f4
Source dataset
uspto-grants-1985_01
Patent number
US04491585

Reaction notes

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