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

반응식

HRID 544441 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ec9ce7cad0d84bfcb864028692f5b823
출처 데이터셋
uspto-grants-1984_05
특허 번호
US04450169

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