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

反応式

HRID 544441 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ec9ce7cad0d84bfcb864028692f5b823
出典データセット
uspto-grants-1984_05
特許番号
US04450169

関連ノート

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