Potassium Carbonate → Methyl 6-(2-morpholinoethoxy)benzofuran-2-carboxylate

HRID 252855

Reaktionsgleichung

Reaktionsgleichung von HRID 252855
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[CH:6]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[O:8][C:4]=2[CH:3]=1.Cl[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CC(C)=O>[O:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][O:1][C:2]2[CH:14]=[CH:13][C:5]3[CH:6]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[O:8][C:4]=3[CH:3]=2)[CH2:19][CH2:20]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 767274-(2-Chloroethyl)morpholineHCID 12082972Methyl 6-hydroxy-1-benzofuran-2-carboxylate

Produkt 1

HCID 59736920Methyl 6-(2-morpholinoethoxy)benzofuran-2-carboxylateAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18184436N,N-dimethylformamide acetoneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of 267 (650 mg, 3.39 mmol) in a 1:1 mixture of DMF-acetone (20 mL) was added 4-(2-chloroethyl)morpholine (630 mg, 3.39 mmol) and potassium carbonate (937 mg, 6.78 mmol). The reaction mixture was stirred at 60° C. for 72 hours. The solvents were removed under reduced pressure and water (50 mL) was added to the residue. 2M Sodium carbonate solution (20 mL) was added and the resultant solution was extracted with ethyl acetate (2×40 mL). The organic phase was separated, dried with sodium sulfate and the solvents removed under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 1:1 ethyl acetate-hexanes, then ethyl acetate, then 9:1 ethyl acetate-methanol. This afforded 268 as a clear oil (760 mg, 73% yield). 1H NMR: (DMSO) δ 7.67-7.63 (m, 2H), 7.32 (s, 1H), 6.98 (d, J=8.5 Hz, 1H), 4.14-4.16 (m, 2H), 3.85 (s, 3H), 3.57-3.55 (m, 4H), 2.88-2.86 (m, 2H), 2.72-2.70 (m, 4H).

Aufarbeitung

  1. customThe solvents were removed under reduced pressure and water (50 mL)
  2. additionwas added to the residue
  3. addition2M Sodium carbonate solution (20 mL) was added
  4. extractionthe resultant solution was extracted with ethyl acetate (2×40 mL)
  5. customThe organic phase was separated
  6. dry with materialdried with sodium sulfate
  7. customthe solvents removed under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluting with a gradient of 1:1 ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-954b34f0d0124745931cb1bf0a2476fd
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868205B2

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