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

HRID 1913760노트

반응식

HRID 1913760 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]benzoate수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0b29134c912d44e0abfa1ac082360327
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609727B2

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