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

HRID 1913760ノート

反応式

HRID 1913760 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収率 83%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

20.6 ml (20.6 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 reaction mixture is stirred at this temperature for 3 hours. Then a further 10 ml (10 mmol) of 1 M borane-THF complex solution are added dropwise, and the mixture is stirred at −15° C. for a further 30 min. After reaction is complete, saturated sodium bicarbonate solution is added to the reaction mixture, and the solvent is evaporated to dryness. The residue is taken up in dichloromethane, dried over sodium sulphate and again freed of solvent. The resulting crude product is purified by flash chromatography on 150 g of silica gel (mobile phase: ethyl acetate/petroleum ether 1:1). 3.1 g (90% purity, 83% yield) of a colourless solid are obtained.

後処理

  1. additionThen a further 10 ml (10 mmol) of 1 M borane-THF complex solution are added dropwise
  2. stirringthe mixture is stirred at −15° C. for a further 30 min
  3. customAfter reaction
  4. customthe solvent is evaporated to dryness
  5. dry with materialdried over sodium sulphate
  6. customThe resulting crude product is purified by flash chromatography on 150 g of silica gel (mobile phase: ethyl acetate/petroleum ether 1:1)
  7. custom3.1 g (90% purity, 83% yield) of a colourless solid are obtained

出典と根拠

ORDレコード
ord-0b29134c912d44e0abfa1ac082360327
出典データセット
uspto-grants-2013_12
特許番号
US08609727B2

反応ノート

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