Methanol → 4-Methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine

HRID 924398ノート

反応式

HRID 924398 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH2:8][CH2:9][CH2:10][C:3]=12.[CH3:11][OH:12].C[O-].[Na+]>CCOC(C)=O.Cl>[CH3:11][O:12][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH2:8][CH2:9][CH2:10][C:3]=12

参加物

6

反応物 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 122033274-chloro-5H,6H,7H-cyclopenta[b]pyridine

生成物 1

HCID 867266834-Methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine収率 44%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

A mixture of 4-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine (2.8 g, 18 mmol), MeOH (20 mL) and sodium methoxide (3.0 g, 56 mmol) was sealed in a pressurized flask and heated at 110° C. for 18 h. The mixture was diluted with EtOAc and neutralized with HCl to pH=1. The organic solvent was removed under reduced pressure. The resulting mixture was washed with ether twice, and neutralized with aq. Na2CO3. The aqueous layer was extracted twice with EtOAc. The combined organic extracts were dried, filtered and concentrated under reduced pressure to give the sub-title compound (1.20 g, 44%). LCMS calc. for C9H12NO (M+H)+: m/z=150.3. Found: 150.2.

後処理

  1. customwas sealed in a pressurized flask
  2. customThe organic solvent was removed under reduced pressure
  3. washThe resulting mixture was washed with ether twice
  4. extractionThe aqueous layer was extracted twice with EtOAc
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-001833d127c343ab84b58eecb4e33c70
出典データセット
uspto-grants-2016_03
特許番号
US09278950B2

反応ノート

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