HCID 86615013, Verbindung → 5-(1-Hydroxyethyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester

HRID 732565Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732565
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2].[CH3:21][Mg]Br>C1COCC1>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH:18]([OH:19])[CH3:21])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 86615013HCID 86615013, VerbindungHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 688153185-(1-Hydroxyethyl)-N-methyl-N-propyl-isophthalamic acid ethyl esterAusbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Treat a solution of 5-formyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (400 mg, 1.44 mmol) in THF (10 mL) at 0° C. with methylmagnesium bromide (3.0 M in diethyl ether, 0.58 mL, 1.73 mmol). Stir at 0° C. for 1 h and quench with saturated aqueous ammonium chloride solution. Extract with ethyl acetate (100 mL), dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 40:60 to 70:30 ethyl acetate:hexanes) to give the title compound (250 mg, 59%).

Aufarbeitung

  1. customquench with saturated aqueous ammonium chloride solution
  2. extractionExtract with ethyl acetate (100 mL)
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 40:60 to 70:30 ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a35ab8fdb5864cc8bc7a88fbac9f2a5d
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585885B2

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