Sodium Bicarbonate → Methyl 4-[3-(4-cyanobenzyl)-4-hydroxybutyl]benzoate
Reaktionsgleichung
[C:1]([CH:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)[CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)(O)=[O:2].C(=O)(O)[O-].[Na+]>C1COCC1>[C:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][CH:4]([CH2:1][OH:2])[CH2:5][CH2:6][C:7]2[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=2)=[CH:23][CH:22]=1)#[N:25]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -5 °C
Versuchsvorschrift
47.43 ml (47.43 mmol) of a 1 M borane-THF complex solution are added dropwise to a solution of 8 g (23.71 mmol) of methyl 4-[3-carboxy-4-(4-cyanophenyl)butyl]benzoate from Example 47A in 200 ml of THF at −10° C. After the mixture has warmed to −5° C. it is stirred at this temperature for 4 h. After the reaction is complete, the reaction mixture is mixed with saturated sodium bicarbonate solution and the solvent is evaporated to dryness. The residue is taken up in dichloromethane, dried over sodium sulphate and, after filtration, again freed of solvent. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:10). 5.8 g (98% purity, 74% of theory) of a colourless solid are obtained.
Aufarbeitung
- customthe solvent is evaporated to dryness
- dry with materialdried over sodium sulphate
- filtrationafter filtration
- customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:10)
- custom5.8 g (98% purity, 74% of theory) of a colourless solid are obtained
Quellen und Nachweise
- ORD-Eintrag
- ord-e85cf9f462104ced98911a8a24e5c065
- Quelldatensatz
- uspto-grants-2013_12
- Patentnummer
- US08609727B2
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