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

HRID 2409152ノート

反応式

HRID 2409152 の反応式
[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[C:5]2[CH2:10][CH2:9][CH2:8][C:6]=2[CH:7]=1.[C:12]([O:15]C(=O)C)(=[O:14])[CH3:13]>>[C:12]([O:15][CH:10]1[C:5]2[N:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=2[CH2:8][CH2:9]1)(=[O:14])[CH3:13]

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収率 71%

実験手順

A solution of 3-chloro-6,7-dihydro-5H-cyclopentapyridine 1-oxide (1 g, 5.9 mmole) in acetic anhydride (30 ml) was heated to 110° C. and stirred at this temperature for 20 h. The solvent was evaporated and the residue was partitioned between aqueous saturated NaHCO3 solution and dichloromethane. The organic layer was dried, evaporated and the residue was purified by flash chromatography over silica using EtOAc/n-heptane (gradient from 0% to 30% EtOAc) to give the title compound as a red liquid (880 mg, 71% yield). MS (ESI): m/z=212.0 [M+H]+.

後処理

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between aqueous saturated NaHCO3 solution and dichloromethane
  3. customThe organic layer was dried
  4. customevaporated
  5. customthe residue was purified by flash chromatography over silica

出典と根拠

ORDレコード
ord-39131da47a5749b8a69f5a6f50f6c980
出典データセット
uspto-grants-2014_08
特許番号
US08815881B2

反応ノート

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