Cyclopropanecarbonyl chloride, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)- → HCID 54475365, compound

HRID 582737Notes

Reaction equation

HRID 582737 reaction equation
[CH2:1]([C:3]1[CH2:4][CH:5]([OH:8])[CH2:6][CH:7]=1)[CH3:2].[CH3:9][C:10]1([CH3:20])[C@@H:12]([CH:13]=[C:14]([Cl:16])[Cl:15])[C@H:11]1[C:17](Cl)=[O:18].C(C1CC(O)CC=1C)C.Cl/C(/C(F)(F)F)=C\[C@@H]1[C@H](C(Cl)=O)C1(C)C>>[CH3:9][C:10]1([CH3:20])[C@@H:12]([CH:13]=[C:14]([Cl:15])[Cl:16])[C@H:11]1[C:17]([O:8][CH:5]1[CH2:6][CH:7]=[C:3]([CH2:1][CH3:2])[CH2:4]1)=[O:18]

Participants

5

Reactant 4

HCID 10966240Cyclopropanecarbonyl chloride, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)-HCID 11334477(1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chlorideHCID 15869648(RS)-3-ethyl-4-methyl-3-cyclopenten-1-olHCID 54217227(RS)-3-ethyl-3-cyclopenten-1-ol

Product 1

HCID 54475365HCID 54475365, compoundYield 85.1%

Procedure

(RS)-3-ethyl-3-cyclopenten-1-ol (500 mg) and (1R)-cis-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarbonyl chloride (1014 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-ethyl-3-cyclopentenyl (1R)-cis-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate (Compound No. 132). Yield 80% nD25 1.5063

Workup

  1. customthe reaction procedures

Sources & evidence

ORD record
ord-84e823862b7e4050b69eb3742de4f6a8
Source dataset
uspto-grants-1999_07
Patent number
US05925676

Reaction notes

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