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

HRID 1672617Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1672617
[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]benzoateAusbeute 57,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

24.28 ml of a 1 M borane-THF complex solution (24.28 mmol) are added dropwise to a solution of 5.32 g (77% purity, 12.14 mmol) of methyl 4-[2-carboxy-4-(4-cyanophenyl)butyl]benzoate from Example 14A in 40 ml of THF at −15° C., and the solution is stirred at this temperature for 4 h. 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, after filtration, again freed of solvent. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). 2.25 g (55% yield) of a colorless solid are obtained.

Aufarbeitung

  1. customAfter reaction
  2. concentrationthe solvent is concentrated to dryness
  3. dry with materialdried over sodium sulfate
  4. filtrationafter filtration
  5. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-e965281d497a40c09a674a3510033bbe
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998988B2

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