Borane → (2-Methyl-4-nitrophenyl)methanol

HRID 469836ノート

反応式

HRID 469836 の反応式
[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].B.C1COCC1.B.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]

参加物

6

反応物 4

HCID 6331BoraneHCID 11430Potassium CarbonateHCID 747904-Nitro-o-toluic acidHCID 2723981Borane;tetrahydrofuran

生成物 1

HCID 21345674(2-Methyl-4-nitrophenyl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5.08 g (27.2 mmol) 2-methyl-4-nitrobenzoic acid in 50 ml dry THF, 41 ml (41 mmol) borane-THF complex (1M solution in THF) is added drop-wise at 0° C. After completion of the borane addition, the reaction mixture is stirred at room temperature for 20 h. After that a K2CO3 solution (1.33 g in 49 ml water) is slowly added under stirring. Then the reaction mixture is poured on water and extracted 3× with EtOAc. The combined organic layers are washed with water and saturated NaCl solution, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is taken up in diethylether, vigorously stirred, and the title compound is obtained after filtration as a yellow crystalline solid.

後処理

  1. stirringunder stirring
  2. additionThen the reaction mixture is poured on water
  3. extractionextracted 3× with EtOAc
  4. washThe combined organic layers are washed with water and saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated in vacuo
  8. stirringvigorously stirred

出典と根拠

ORDレコード
ord-76c24169e53a4c4699c20463670903bc
出典データセット
uspto-grants-2014_01
特許番号
US08629168B2

反応ノート

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