Morpholine → Acetic acid 6,7-dimethyl-2-(2-morpholin-4-yl-acetyl)-benzofuran-5-yl ester

HRID 480980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 480980
Br[CH2:2][C:3]([C:5]1[O:6][C:7]2[C:13]([CH3:14])=[C:12]([CH3:15])[C:11]([O:16][C:17](=[O:19])[CH3:18])=[CH:10][C:8]=2[CH:9]=1)=[O:4].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:15][C:12]1[C:11]([O:16][C:17](=[O:19])[CH3:18])=[CH:10][C:8]2[CH:9]=[C:5]([C:3](=[O:4])[CH2:2][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[O:6][C:7]=2[C:13]=1[CH3:14]

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 101719982-Bromo-1-(5-acetoxy-6,7-dimethyl-benzofuran-2-yl)-ethanone

Produkt 1

HCID 10236780Acetic acid 6,7-dimethyl-2-(2-morpholin-4-yl-acetyl)-benzofuran-5-yl esterAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of 2-bromo-1-(5-acetoxy-6,7-dimethyl-benzofuran-2-yl)-ethanone (47 mg) from Example 16, morpholine (15 mg), and potassium carbonate (25 mg) in acetone (10 mL) was stirred at room temperature for 30 min. It was then evaporated to dryness, and the residue was purified by silica gel column eluting with 5% MeOH in DCM to give 43 mg of acetic acid 6,7-dimethyl-2-(2-morpholin-4-yl-acetyl)-benzofuran-5-yl ester as an oil. Conversion into the HCl salt gave a yellow solid. 1H NMR (CDCl3, 300 MHz) δ: 7.60 (s, 1H), 7.20 (s, 1H), 3.78 (s+t, 6H), 2.64 (m, 4H), 2.50 (s, 3H), 2.40 (s, 3H), 2.20 (s, 3H) ppm. 13C NMR (CD3OD, 75 MHz) (as HCl salt) δ: 180.94, 170.31, 153.65, 150.33, 147.19, 131.94, 124.33, 122.34, 116.04, 113.59, 63.74, 60.89, 53.28, 19.64, 12.18, 12.22 ppm. M/S 332 (M+H+).

Aufarbeitung

  1. customIt was then evaporated to dryness
  2. customthe residue was purified by silica gel column
  3. washeluting with 5% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-269dfb18ece745c2a7cc5eb8a44fcad7
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653346B1

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