Sodium borohydride → [2-(Trifluoromethyl)pyridin-3-yl]methanol

HRID 577192ノート

反応式

HRID 577192 の反応式
[BH4-].[Na+].[F:3][C:4]([F:16])([F:15])[C:5]1[C:10]([C:11](OC)=[O:12])=[CH:9][CH:8]=[CH:7][N:6]=1>C1COCC1>[F:16][C:4]([F:3])([F:15])[C:5]1[C:10]([CH2:11][OH:12])=[CH:9][CH:8]=[CH:7][N:6]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 18374285Methyl 2-(trifluoromethyl)nicotinate

生成物 1

HCID 14761465[2-(Trifluoromethyl)pyridin-3-yl]methanol収率 90.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of sodium borohydride (0.24 g, 6.32 mmol) in anhydrous THF (40 mL) at 0° C. was added dropwise a solution of methyl 2-(trifluoromethyl)pyridine-3-carboxylate (650 mg, 3.16 mmol) in THF (50 mL). After stirring for 1 hour, the reaction mixture was slowly quenched with 15% NaOH and then diluted with water. Ethyl acetate was added, the reaction mixture was stirred for 10 minutes, and the precipitated white solid was filtered off. The solid was washed with ethyl acetate (3×100 mL). The organic layer was separated, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated to provide [2-(trifluoromethyl)pyridin-3-yl]methanol as a thick oil (0.505 g, 90% yield), which was used for the next step without any further purification; M+ 177.1.

後処理

  1. customthe reaction mixture was slowly quenched with 15% NaOH
  2. additiondiluted with water
  3. additionEthyl acetate was added
  4. stirringthe reaction mixture was stirred for 10 minutes
  5. filtrationthe precipitated white solid was filtered off
  6. washThe solid was washed with ethyl acetate (3×100 mL)
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customThe filtrate was evaporated

出典と根拠

ORDレコード
ord-dbe4792b312c4403b800904650418ddd
出典データセット
uspto-grants-2015_05
特許番号
US09040538B2

反応ノート

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