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

HRID 271455노트

반응식

HRID 271455 반응식
[CH3:1][C:2]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].CCOC(C)=O>C1COCC1.O>[CH3:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:8][CH:9]=[C:10]([C:12]([F:14])([F:13])[F:15])[N:11]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 9357Potassium Sodium TartrateHCID 2779428Methyl 2-methyl-6-(trifluoromethyl)nicotinateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 2760122(2-Methyl-6-(trifluoromethyl)pyridin-3-yl)methanol수율 98.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To the solution of methyl 2-methyl-6-(trifluoromethyl)nicotinate (8.8 g, 40 mmol) in 40 mL dry THF at 0° C. under argon was added 1.0 M lithium aluminum hydride in THF solution (40 mL, 40 mmol) drop-wise over 15 min. The reaction mixture was allowed to warm to room temperature over 1 h. HPLC/MS analysis indicated that the reaction was complete. Rochelle's salt, 10% aqueous solution (20 mL) was carefully added to the stirring reaction mixture over a period of 10 min. After 1 h of subsequent stirring, 50 mL EtOAc and water were added. The layers were separated. The organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to obtain 7.5 g of the title compound as a colorless oil, which was greater than 98% pure. HPLC/MS: retention time=2.1 min, [M+H]30 =192.

후처리

  1. customThe layers were separated
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-e8edef4ea77542828c1f80b53c910184
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452892B2

반응 노트

불러오는 중…