Pyridine → HCID 86738497, compound

HRID 1759210Notes

Reaction equation

HRID 1759210 reaction equation
[CH3:1][C:2]1[C:7]([N:8]2[CH:12]=[CH:11][CH:10]=[CH:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:13][OH:14].N1C=CC=CC=1.[Cl:21][C:22]([C:32]([F:35])([F:34])[F:33])=[CH:23][C@@H:24]1[C@H:26]([C:27](Cl)=[O:28])[C:25]1([CH3:31])[CH3:30].CCCCCCC>C1(C)C=CC=CC=1>[Cl:21][C:22]([C:32]([F:33])([F:34])[F:35])=[CH:23][C@@H:24]1[C@H:26]([C:27]([O:14][CH2:13][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([N:8]3[CH:12]=[CH:11][CH:10]=[CH:9]3)[C:2]=2[CH3:1])=[O:28])[C:25]1([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8900HeptaneHCID 155817552-Methyl-3-(1H-pyrrol-1-yl)benzenemethanolHCID 86737382cis-3-(2-Chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarbonyl chloride

Product 1

HCID 86738497HCID 86738497, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

A stirred solution of 2.0 grams (0.011 mole) of 2-methyl-3-(pyrrol-1-yl)phenylmethanol (prepared in Example 2), and 0.9 gram (0.011 mole) of pyridine in 30 ml of toluene was warmed to 50° C. Under a dry-nitrogen atmosphere 2.8 grams (0.011 mole) of cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride in 2 ml of toluene was added in one portion. The addition caused an exothermic reaction which raised the reaction mixture temperature from 50° C. to 55° C. Upon complete addition the reaction mixture was heated to 60° C. where it was stirred for 2.5 hours. The reaction mixture was cooled and poured into a separatory funnel with 300 ml of heptane. The resultant organic layer was washed with 100 ml of an aqueous solution of 2 N hydrochloric acid then with 200 ml of an aqueous solution of 2 N sodium hydroxide. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was purified by distillation using a Kugelrohr distilling system to give 3.8 grams of [2-methyl-3-(pyrrol-1-yl)phenyl]methyl cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate, bp 135° C./0.04 mm.

Workup

  1. additionwas added in one portion
  2. additionThe addition
  3. customan exothermic reaction which
  4. temperatureraised the reaction mixture temperature from 50° C. to 55° C
  5. additionUpon complete addition the reaction mixture
  6. temperatureThe reaction mixture was cooled
  7. washThe resultant organic layer was washed with 100 ml of an aqueous solution of 2 N hydrochloric acid
  8. dry with materialThe organic layer was dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  11. distillationThe oil was purified by distillation
  12. distillationdistilling system

Sources & evidence

ORD record
ord-cab9c0ca150b4cd9bfa76f9757314ca7
Source dataset
uspto-grants-1982_07
Patent number
US04339457

Reaction notes

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