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

HRID 271460노트

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HRID 271460 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0e3555c68a804dab8810b6c913994195
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452892B2

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