Pyridine → HCID 86754275, compound

HRID 582730Notes

Reaction equation

HRID 582730 reaction equation
[CH2:1]([C:4]1[CH2:5][CH:6]([OH:10])[CH2:7][C:8]=1[CH3:9])[CH:2]=[CH2:3].N1C=CC=CC=1.[Cl:17]/[C:18](/[C:28]([CH2:33][F:34])([CH2:31][F:32])[CH2:29][F:30])=[CH:19]\[C@@H:20]1[C@H:22]([C:23](Cl)=[O:24])[C:21]1([CH3:27])[CH3:26]>C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.C1(C)C=CC=CC=1>[Cl:17]/[C:18](/[C:28]([CH2:33][F:34])([CH2:29][F:30])[CH2:31][F:32])=[CH:19]\[C@@H:20]1[C@H:22]([C:23]([O:10][CH:6]2[CH2:7][C:8]([CH3:9])=[C:4]([CH2:1][CH:2]=[CH2:3])[CH2:5]2)=[O:24])[C:21]1([CH3:26])[CH3:27]

Participants

6

Reactant 3

HCID 1049PyridineHCID 54075418(RS)-3-allyl-4-methyl-3-cyclopenten-1-olHCID 86754276HCID 86754276, compound

Product 1

HCID 86754275HCID 86754275, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 314042,6-Di-tert-butyl-4-methylphenolCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of (RS)-3-(2-propenyl)-4-methyl-3-cyclopenten-1-ol (190 mg), 2,6-di-tert-butyl-4-methylphenol (5 mg), pyridine (140 mg) and toluene (10 ml), (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoromethyl-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride (353 mg) was added under ice-cooling. The resulting reaction mixture was further allowed to react for 8 hours at room temperature. Then the reaction mixture was subjected to the same post-treatment as in Example 1 to afford 382 mg of (RS)-3-(2-propenyl)-4-methyl-3-cyclopenten-1-yl (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoromethyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylate (Compound No. 34). Yield 77% nD24 1.4721

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. customThe resulting reaction mixture
  4. customto react for 8 hours at room temperature

Sources & evidence

ORD record
ord-2d161200da004021b3093eb2aad571ae
Source dataset
uspto-grants-1999_07
Patent number
US05925676

Reaction notes

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