Busulfan → Methyl 2-cyano-3-(4-hydroxyphenyl)propanoate

HRID 922186

Reaktionsgleichung

Reaktionsgleichung von HRID 922186
[C:1]([CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5])#[N:2].[CH3:15]S(OCCCCOS(C)(=O)=O)(=O)=O>CO>[C:1]([CH:3]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)[C:4]([O:6][CH3:15])=[O:5])#[N:2]

Komponenten

4

Edukt 2

HCID 2478BusulfanHCID 19379218HCID 19379218, Verbindung

Produkt 1

HCID 22988437Methyl 2-cyano-3-(4-hydroxyphenyl)propanoateAusbeute 55,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a 25 mL RB flask fitted with magnetic stirrer was charged 10 mL of methanol. To the stirred solvent was added 2-cyano-3-(4-hydroxy-phenyl)-propanoic acid (0.5 g, 2.62 mmol), followed by methanesulfonic aid (0.5 mL, 7.69 mmol). After addition, the RM was refluxed at 65° C. for 1 h. After 1 h, the solvent was evaporated, water (20 mL) was added and the organic layer was extracted with ethyl acetate (15 mL×2). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as brown liquid. (0.3 g, yield: 55.8%): MS (ESI, 120 eV): m/z=204.1 (M−H)+.

Aufarbeitung

  1. customTo a 25 mL RB flask fitted with magnetic stirrer
  2. additionAfter addition
  3. customthe solvent was evaporated
  4. additionwater (20 mL) was added
  5. extractionthe organic layer was extracted with ethyl acetate (15 mL×2)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. customthe solvent was removed under reduced pressure
  8. customThe product was obtained as brown liquid

Quellen und Nachweise

ORD-Eintrag
ord-f7d72caff9e245f8996988fb2ce959a6
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278915B2

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