Sodium Bicarbonate → Methyl 4-[4-(4-cyanophenyl)-2-hydroxymethylbutyl]benzoate

HRID 1927392ノート

反応式

HRID 1927392 の反応式
[C:1]([CH:4]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)[CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)(O)=[O:2].C(=O)(O)[O-].[Na+]>C1COCC1>[C:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][CH2:16][CH:4]([CH2:1][OH:2])[CH2:5][C:6]2[CH:7]=[CH:8][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:14][CH:15]=2)=[CH:23][CH:22]=1)#[N:25]

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 57831396Methyl 4-[2-carboxy-4-(4-cyanophenyl)butyl]benzoate

生成物 1

HCID 57831349Methyl 4-[4-(4-cyanophenyl)-2-hydroxymethylbutyl]benzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

26 ml (26 mmol) of a 1 M borane-THF complex solution are added dropwise to a solution of 4.2 g (12.98 mmol) of methyl 4-[2-carboxy-4-(4-cyanophenyl)butyl]benzoate in 40 ml of THF at −15° C., and the mixture is stirred at this temperature for 3 h. A further 13 ml (13 mmol) of 1 M borane-THF complex solution is then added dropwise and stirring is continued for a further 30 min at −15° C. After reaction is complete, saturated sodium bicarbonate solution is added to the reaction mixture, and the solvent is concentrated to dryness. The residue is taken up in dichloromethane, dried over sodium sulfate and again freed of solvent. The resulting crude product is purified by flash chromatography (mobile phase: ethyl acetate/petroleum ether 1:1, 150 g silica gel). 3.1 g (90% purity, 83% of theory) of a colorless solid are obtained.

後処理

  1. additionA further 13 ml (13 mmol) of 1 M borane-THF complex solution is then added dropwise
  2. stirringstirring
  3. waitis continued for a further 30 min at −15° C
  4. customAfter reaction
  5. concentrationthe solvent is concentrated to dryness
  6. dry with materialdried over sodium sulfate
  7. customThe resulting crude product is purified by flash chromatography (mobile phase: ethyl acetate/petroleum ether 1:1, 150 g silica gel)
  8. custom3.1 g (90% purity, 83% of theory) of a colorless solid are obtained

出典と根拠

ORDレコード
ord-a37fd1e6befa4d18a8ebe084bcaf63a2
出典データセット
uspto-grants-2012_05
特許番号
US08183271B2

反応ノート

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