Pyridine → HCID 53677451, compound

HRID 582731Notes

Reaction equation

HRID 582731 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.[CH3:17][C:18]1([CH3:28])[C@H:20]([CH:21]=[C:22]([Cl:24])[Cl:23])[C@H:19]1[C:25](Cl)=[O:26]>C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.C1(C)C=CC=CC=1>[CH3:17][C:18]1([CH3:28])[C@H:20]([CH:21]=[C:22]([Cl:23])[Cl:24])[C@H:19]1[C:25]([O:10][CH:6]1[CH2:7][C:8]([CH3:9])=[C:4]([CH2:1][CH:2]=[CH2:3])[CH2:5]1)=[O:26]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6454308(1R,3S)-3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chlorideHCID 54075418(RS)-3-allyl-4-methyl-3-cyclopenten-1-ol

Product 1

HCID 53677451HCID 53677451, compoundYield 84.5%

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), (1R)-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarbonyl chloride (310 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 379 mg of (RS)-3-(2-propenyl)-4-methyl-3-cyclopenten-1-yl (1R)-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate (Compound No. 18). Yield 77% nD24 1.5112

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-e7508c7d2505469fb8a4993ef89070f2
Source dataset
uspto-grants-1999_07
Patent number
US05925676

Reaction notes

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