Neopentyl alcohol → 2,2-Dimethylpropyl 6-chloropyridine-3-carboxylate

HRID 45249

反応式

HRID 45249 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](Cl)=[O:9])=[CH:4][CH:3]=1.[CH3:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14]>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH3:11])=[O:9])=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 6404Neopentyl alcoholHCID 27821656-Chloronicotinoyl Chloride

生成物 1

HCID 866597462,2-Dimethylpropyl 6-chloropyridine-3-carboxylate収率 92%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a solution of 10 g (56.8 mmol) of 6-chloropyridine-3-carbonyl chloride in 100 mL of anhydrous toluene are added under argon, at room temperature, 15 g (170.4 mmol) of 2,2-dimethylpropanol. The reaction medium is then heated for 6 hours at 80° C. After cooling to room temperature, the medium is concentrated and the residue obtained is taken up in 800 mL of EtOAc, washed successively with water (2×200 mL), saturated NaHCO3 solution (2×200 mL) and brine (100 mL), dried over Na2SO4, and then concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 5% EtOAc. 11.9 g of 2,2-dimethylpropyl 6-chloropyridine-3-carboxylate are obtained in the form of a white powder.

後処理

  1. temperatureAfter cooling to room temperature
  2. concentrationthe medium is concentrated
  3. customthe residue obtained
  4. washwashed successively with water (2×200 mL), saturated NaHCO3 solution (2×200 mL) and brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. custompurified by chromatography on a column of silica gel
  8. washeluting with a cyclohexane/EtOAc gradient of 0 to 5% EtOAc

出典と根拠

ORDレコード
ord-095d32159f074af9a6090351ff177e40
出典データセット
uspto-grants-2013_09
特許番号
US08541455B2

関連ノート

読み込み中…