Acetic Anhydride → 3-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl Acetate

HRID 403255ノート

反応式

HRID 403255 の反応式
[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1.[C:12]([O:15]C(=O)C)(=[O:14])[CH3:13]>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([O:15][C:12](=[O:14])[CH3:13])[CH2:7][CH2:8][C:9]=2[CH:10]=1

参加物

3

反応物 2

HCID 7918Acetic AnhydrideHCID 580828393-Chloro-6,7-dihydro-5h-cyclopenta[b]pyridine 1-oxide

生成物 1

HCID 580827683-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl Acetate

実験手順

A solution of 3-chloro-6,7-dihydro-5H-[1]pyrindine 1-oxide (2.07 g, 12.2 mmol) in acetic acid anhydride (62.2 ml, 659 mmol) was stirred at 110° C. for 20 hours. For the workup, the solvent was removed at reduced pressure and the residue quenched with saturated aqueous solution of sodium hydrogen carbonate. The aqueous phase was extracted with dichloromethane, the resulting organic layers combined and dried over sodium sulfate. After evaporation of the solvent, the residue was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 70:30 as the eluent. The acetic acid 3-chloro-6,7-dihydro-5H-[1]pyrindin-7-yl ester was obtained as a red liquid (1.57 g, 61%); (calculated) C10H10ClNO2 [211.65]; (found) [M+H]+=212.

後処理

  1. customFor the workup, the solvent was removed at reduced pressure
  2. customthe residue quenched with saturated aqueous solution of sodium hydrogen carbonate
  3. extractionThe aqueous phase was extracted with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 70:30 as the eluent

出典と根拠

ORDレコード
ord-70a89fe382ab49d6a575d15fe3adb4be
出典データセット
uspto-grants-2014_06
特許番号
US08748418B2

反応ノート

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