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

HRID 1927392노트

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HRID 1927392 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a37fd1e6befa4d18a8ebe084bcaf63a2
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183271B2

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