N-methyl-2-pyrrolidone → Methyl 2,4-diethylbenzoate

HRID 1256197

Reaktionsgleichung

Reaktionsgleichung von HRID 1256197
Cl[C:2]1[CH:11]=[C:10](Cl)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CN1CC[CH2:16][C:15]1=O.[CH2:20]([Mg]Br)[CH3:21]>O1CCCC1>[CH2:15]([C:2]1[CH:11]=[C:10]([CH2:20][CH3:21])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH3:16]

Komponenten

5

Edukt 3

HCID 13387N-methyl-2-pyrrolidoneHCID 37055Methyl 2,4-dichlorobenzoateHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 66741803Methyl 2,4-diethylbenzoateAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of Fe(acac)3 (0.34 g, 0.96 mmol), methyl 2,4-dichlorobenzoate (4.0 g, 19.6 mmol), and N-methyl-2-pyrrolidinone (8 mL) in THF (100 mL) at −20° C. under nitrogen was added a tetrahydrofuran (THF) solution (1.0 M) of ethylmagnesium bromide (40.0 mL, 40.0 mmol) over a period of −5 min. The resulting mixture was stirred while gradually warming to ambient temperature. Stirring was continued for an additional 17 h. The reaction mixture was partitioned between water and dichloromethane. The organic layer was separated, washed with brine, dried (MgSO4), and pumped to dryness under reduced pressure. The brown residue was purified by column chromatography (SiO2, 20% EtOAc/heptane) to give 1.2 g of the desired product as a clear oil (yield of 32%), along with 1.1 g of methyl 4-ethylbenzoate. 1H NMR (300 MHz, DMSO-d6) δ 1.15 (t, 3H), 1.20 (t, 3H), 2.66 (q, 2H), 2.92 (q, 2H), 3.82 (s, 3H), 7.15 (d, 1H), 7.23 (s, 1H), 7.76 (d, 1H).

Aufarbeitung

  1. stirringStirring
  2. customThe reaction mixture was partitioned between water and dichloromethane
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customThe brown residue was purified by column chromatography (SiO2, 20% EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-df7fc28527434d7ea26309fb34a639e8
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461153B2

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