Citric Acid → HCID 86754273, compound

HRID 582727Notes

Reaction equation

HRID 582727 reaction equation
[CH2:1]([C:3]1[CH2:4][CH:5]([OH:9])[CH2:6][C:7]=1[CH3:8])[CH3:2].N1C=CC=CC=1.[Cl:16]/[C:17](/[C:27]([F:30])([F:29])[F:28])=[CH:18]\[C@@H:19]1[C@H:21]([C:22](Cl)=[O:23])[C:20]1([CH3:26])[CH3:25].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.C1(C)C=CC=CC=1>[Cl:16]/[C:17](/[C:27]([F:28])([F:29])[F:30])=[CH:18]\[C@@H:19]1[C@H:21]([C:22]([O:9][CH:5]2[CH2:6][C:7]([CH3:8])=[C:3]([CH2:1][CH3:2])[CH2:4]2)=[O:23])[C:20]1([CH3:26])[CH3:25]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 1049PyridineHCID 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-ol

Product 1

HCID 86754273HCID 86754273, compoundYield 83%

Reagents, catalysts & solvents 2

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

Procedure

To a mixture of (RS)-3-ethyl-4-methyl-3-cyclopenten-1-ol (115 mg), 2,6-di-tert-butyl-4-methylphenol (5 mg), pyridine (92 mg) and toluene (10 ml), (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride (238 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 poured into ice-cooled 5% aqueous solution of citric acid and extracted three times with diethyl ether. After the combined ether layer was washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution and dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (eluent; n-hexane/ethyl acetate=30/1) to afford 265 mg of (RS)-3-ethyl-4-methyl-3-cyclopenten-1-yl (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate (Compound No. 11). Yield 83% nD27 1.4645

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. customThe resulting reaction mixture
  4. customto react for 8 hours at room temperature
  5. additionThen the reaction mixture was poured into ice-
  6. extractionextracted three times with diethyl ether
  7. washAfter the combined ether layer was washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-17b54628c53c4b1e90ecb374ed18a327
Source dataset
uspto-grants-1999_07
Patent number
US05925676

Reaction notes

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