Ethyl Acetate → 5-Chloro-2-(3-methoxypropyl)pyridine-4-carbaldehyde

HRID 2428092ノート

反応式

HRID 2428092 の反応式
[Cl:1][C:2]1[C:3]([CH:13](OC)[O:14]C)=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][CH3:12])=[N:6][CH:7]=1.CCOC(C)=O.[OH-].[Na+]>Cl>[Cl:1][C:2]1[C:3]([CH:13]=[O:14])=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][CH3:12])=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 667628875-Chloro-4-(dimethoxymethyl)-2-(3-methoxypropyl)pyridine

生成物 1

HCID 714237335-Chloro-2-(3-methoxypropyl)pyridine-4-carbaldehyde収率 99.9%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
80 °C

実験手順

5-Chloro-4-dimethoxymethyl-2-(3-methoxy-propyl)-pyridine (25.5 g, 98.2 mmol) was dissolved in aq. 1M HCl (500 mL), and the mixture was heated to 80° C. for 2 h. The mixture was allowed to cool to rt, and EtOAc was added. The mixture was cooled to 0° C., and was basified with aq. 2.5M NaOH to pH=10. The layers were separated, and the org. layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (98.1 mmol, 99%) that was used further without purification. LC-MS: tR=0.62 min; ES+: 246.12.

後処理

  1. temperatureto cool to rt
  2. temperatureThe mixture was cooled to 0° C.
  3. customThe layers were separated
  4. dry with materiallayer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customDrying the residue under high vacuum

出典と根拠

ORDレコード
ord-f30bcd5c19084a86a7401744f0f9ac7e
出典データセット
uspto-grants-2011_06
特許番号
US07968720B2

反応ノート

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