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

HRID 1927392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927392
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a37fd1e6befa4d18a8ebe084bcaf63a2
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183271B2

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