Benzyl Alcohol → 1-[6-(Benzyloxy)pyridin-3-yl]cyclopropanecarboxylic acid

HRID 504319ノート

反応式

HRID 504319 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:11]([O:13]CC)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:16]([OH:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Na+]>C(OCC)(=O)C>[CH2:16]([O:23][C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=[O:12])[CH2:9][CH2:10]2)=[CH:4][CH:3]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydride2 回HCID 86602273Ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate

生成物 1

HCID 666616601-[6-(Benzyloxy)pyridin-3-yl]cyclopropanecarboxylic acid

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate (45.1 mg, 0.000200 mol), benzyl alcohol (0.50 mL, 0.0048 mol) and sodium hydride (9.50 mg, 0.000238 mol) was irradiated by microwave at 150° C. for 15 minutes. After cooling, additional sodium hydride (9.5 mg) was added to the mixture. The mixture then was irradiated by microwave at 150° C. for 15 minutes. Ethyl acetate (5 mL) was added and the resulting mixture was washed with water and brine successively. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by Combiflash with ethyl acetate/hexane to give the desired product.

後処理

  1. customwas irradiated by microwave at 150° C. for 15 minutes
  2. temperatureAfter cooling
  3. customThe mixture then was irradiated by microwave at 150° C. for 15 minutes
  4. washthe resulting mixture was washed with water and brine successively
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by Combiflash with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-0460f591c58948519b083d1681c1fc23
出典データセット
uspto-grants-2010_08
特許番号
US07776874B2

反応ノート

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