(1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride → (RS)-3-propyl-3-cyclopentenyl (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 582736Notes

Reaction equation

HRID 582736 reaction equation
[CH2:1]([C:4]1[CH2:5][CH:6]([OH:9])[CH2:7][CH:8]=1)[CH2:2][CH3:3].CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(Cl)=O.C(C1CC(O)CC=1C)C.[Cl:31]/[C:32](/[C:42]([F:45])([F:44])[F:43])=[CH:33]\[C@@H:34]1[C@H:36]([C:37](Cl)=[O:38])[C:35]1([CH3:41])[CH3:40]>>[Cl:31]/[C:32](/[C:42]([F:43])([F:44])[F:45])=[CH:33]\[C@@H:34]1[C@H:36]([C:37]([O:9][CH:6]2[CH2:7][CH:8]=[C:4]([CH2:1][CH2:2][CH3:3])[CH2:5]2)=[O:38])[C:35]1([CH3:41])[CH3:40]

Participants

5

Reactant 4

HCID 11334477(1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chlorideHCID 12617358cis-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropylcarbonyl chlorideHCID 15869648(RS)-3-ethyl-4-methyl-3-cyclopenten-1-olHCID 54345607(RS)-3-propyl-3-cyclopenten-1-ol

Product 1

HCID 86754279(RS)-3-propyl-3-cyclopentenyl (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylateYield 91%

Procedure

(RS)-3-propyl-3-cyclopenten-1-ol (500 mg) and (1RS)-cis-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarbonyl chloride (902 mg) were respectively used instead of (RS)-3-ethyl-4-methyl-3-cyclopenten-1-ol and (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride used in Example 1 above and the reaction procedures were carried out in the same manner as in Example 1 to afford 1150 mg of (RS)-3-propyl-3-cyclopentenyl (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate (Compound No. 130). Yield 91% nD24 1.5038

Workup

  1. customthe reaction procedures

Sources & evidence

ORD record
ord-ad53a2d98b3b40ceb255233960d7d78e
Source dataset
uspto-grants-1999_07
Patent number
US05925676

Reaction notes

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