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

HRID 271455ノート

反応式

HRID 271455 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-e8edef4ea77542828c1f80b53c910184
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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