Ethyl Acetate → (2-Cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)methanol

HRID 271460ノート

反応式

HRID 271460 の反応式
[CH:1]1([C:4]2[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:5]=2[C:6](OC)=[O:7])[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOC(C)=O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[CH:1]1([C:4]2[C:5]([CH2:6][OH:7])=[CH:10][CH:11]=[C:12]([C:14]([F:17])([F:15])[F:16])[N:13]=2)[CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 59834808Methyl 2-cyclopropyl-6-(trifluoromethyl)nicotinate

生成物 1

HCID 59834793(2-Cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)methanol収率 100.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of methyl 2-cyclopropyl-6-(trifluoromethyl)nicotinate (1 g, 4.08 mmol) in THF (6 mL) at 0° C. under argon was added 1.0 M lithium aluminum hydride in THF solution (6 mL, 6.0 mmol). The reaction mixture was stirred at 0° C. for 15 min. EtOAc (20 mL) was added to the reaction mixture, which was then stirred at room temperature for 30 min. A 10% aqueous potassium sodium tartrate solution (20 mL) was added to the reaction mixture and stirring was continued for another 30 min. The organic layer was separated, washed with saturated aqueous NaCl, dried (MgSO4), filtered and concentrated to obtain 890 mg of the title compound as a pale yellow oil. HPLC/MS: retention time=3.055 min, [M+H]+=218.

後処理

  1. stirringwas then stirred at room temperature for 30 min
  2. stirringstirring
  3. waitwas continued for another 30 min
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-0e3555c68a804dab8810b6c913994195
出典データセット
uspto-grants-2008_11
特許番号
US07452892B2

反応ノート

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