Aluminium lithium hydride → {2-[4-(Trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methanol

HRID 891057ノート

反応式

HRID 891057 の反応式
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([C:14](OC)=[O:15])[N:13]=2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=2)=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 22064320Methyl 2-(4-(trifluoromethyl)phenyl)oxazole-4-carboxylate

生成物 1

HCID 22064105{2-[4-(Trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methanol

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

A solution of methyl 2-[4-(trifluoromethyl)phenyl]-1,3-oxazole-4-carboxylate (1.365 mmol) in tetrahydrofuran (20 ml) was cooled to 0° C., and lithium aluminum hydride in tetrahydrofuran (1.365 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 30 minutes, slowly quenched with water, followed by addition of ammonium chloride solution. The resulting mixture was filtered through celite, and washed with ethyl acetate. The filtrate was washed with brine, dried over sodium sulfate, and solvent removed under reduced pressure. The residue was purified by chromatography, to yield {2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methan-1-ol, a compound of formula (16).

後処理

  1. customslowly quenched with water
  2. additionfollowed by addition of ammonium chloride solution
  3. filtrationThe resulting mixture was filtered through celite
  4. washwashed with ethyl acetate
  5. washThe filtrate was washed with brine
  6. dry with materialdried over sodium sulfate, and solvent
  7. customremoved under reduced pressure
  8. customThe residue was purified by chromatography

出典と根拠

ORDレコード
ord-9a04cefd3233442987e57f9e7655436b
出典データセット
uspto-grants-2006_02
特許番号
US07001909B2

反応ノート

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