Water → Methyl 5-cyano-5-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxocyclohexanecarboxylate

HRID 1780828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1780828
[C:1]([C:3]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:17]=1)([CH2:10][CH2:11][C:12]([O:14]C)=O)[CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])#[N:2].[H-].[Na+].O>COCCOC>[C:6]([CH:5]1[CH2:4][C:3]([C:1]#[N:2])([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:17]=2)[CH2:10][CH2:11][C:12]1=[O:14])([O:8][CH3:9])=[O:7]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24758Sodium hydrideHCID 10811164Dimethyl 4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]heptanedioate

Produkt 1

HCID 10959646Methyl 5-cyano-5-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxocyclohexanecarboxylateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a solution of dimethyl 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)pimelate (5.9 g, 14.6 mmol) in dry 1,2-dimethoxyethane (120 mL) under an argon atmosphere was added sodium hydride (80% suspension in mineral oil, 1.05 g, 43.8 mmol). The mixture was heated to reflux for 4.5 h, then was cooled to room temperature and was stirred for 16 h. Water was added and the reaction mixture was partitioned between ether and acidic water. The organic extract was dried (magnesium sulfate) and the solvent was removed in vacuo. The residue was purified by flash chromatography, eluting with 3:1 hexanes/ethyl acetate, to provide a white foam (4.9 g, 93%). Analysis Calc. for C19H23NO3 ·1/4H2O: C 67.09, H 6.84, N 3.72; found: C 66.92, H 6.61, N 3.74.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4.5 h
  3. customthe reaction mixture was partitioned between ether and acidic water
  4. extractionThe organic extract
  5. dry with materialwas dried (magnesium sulfate)
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with 3:1 hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-07472a8d80be4e3f847d435edc014f25
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05631286

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