Potassium Carbonate → [5-phenoxy-(1,2,4)-thiadiazol-3-yl]-methyl (1R,3R)2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane-1-carboxylate

HRID 544441

Reaction equation

HRID 544441 reaction equation
Cl[CH2:2][C:3]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[S:5][N:4]=1.[CH3:15][C:16]1([CH3:26])[C@H:18]([CH:19]=[C:20]([CH3:22])[CH3:21])[C@H:17]1[C:23]([OH:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].O1CCOCCOCCOCCOCCOCC1>C(C(C)=O)C>[CH3:15][C:16]1([CH3:26])[C@H:18]([CH:19]=[C:20]([CH3:21])[CH3:22])[C@H:17]1[C:23]([O:25][CH2:2][C:3]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[S:5][N:4]=1)=[O:24]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 16747chrysanthemic acid d-trans-formHCID 2855718-Crown-6HCID 131061443-Chloromethyl-5-phenoxy-(1,2,4)-thiadiazole

Product 1

HCID 57293778[5-phenoxy-(1,2,4)-thiadiazol-3-yl]-methyl (1R,3R)2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane-1-carboxylateYield 30.9%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4.5 g of 3-chloromethyl-5-phenoxy-(1,2,4)-thiadiazole, 3.7 g of (1R,3R) 2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane-1-carboxylic acid, 50 ml of methyl ethyl ketone, 3.2 g of potassium carbonate and 0.1 gof 1,4,7,10,13,16-hexaoxacyclooctadecane was refluxed for 18 hours and was cooled and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution withbenzene yielded 2.2 g of [5-phenoxy-(1,2,4)-thiadiazol-3-yl]-methyl (1R,3R)2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane-1-carboxylate.

Workup

  1. temperaturewas refluxed for 18 hours
  2. temperaturewas cooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness under reduced pressure
  5. customthe residue was chromatographed over silica gel
  6. washElution withbenzene

Sources & evidence

ORD record
ord-ec9ce7cad0d84bfcb864028692f5b823
Source dataset
uspto-grants-1984_05
Patent number
US04450169

Linked notes

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