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

HRID 2409152노트

반응식

HRID 2409152 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

HCID 580827683-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl Acetate수율 71%

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-39131da47a5749b8a69f5a6f50f6c980
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815881B2

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