Water → {4-[2,4-Bis(methoxymethoxy)phenyl]cyclohexylidene}acetonitrile

HRID 1007963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1007963
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH3:14][O:15][CH2:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][O:26][CH3:27])[CH:21]=[CH:20][C:19]=1[CH:28]1[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1.O>COCCOC.C(OCC)C>[CH3:14][O:15][CH2:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][O:26][CH3:27])[CH:21]=[CH:20][C:19]=1[CH:28]1[CH2:33][CH2:32][C:31](=[CH:5][C:3]#[N:4])[CH2:30][CH2:29]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 121351704-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanone

Produkt 1

HCID 22337767{4-[2,4-Bis(methoxymethoxy)phenyl]cyclohexylidene}acetonitrileAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

To a round bottomed flask equipped was added sodium hydride (40 mg, 60% dispersion in mineral oil) and 1, 2-dimethoxyethane (10 ml). Diethyl cyanomethylphosphonate (102 μl, 0.95 mmol) was added and the reaction mixture allowed to warm to room temperature. 4-[(2,4-Bis(methoxymethoxy)phenyl)]cyclohexanone (200 mg) was added as a solution in 1,2-dimethoxyethane (10 ml) and the reaction mixture stirred for 17 hr at room temperature. The reaction mixture was poured into a separating funnel containing water (50 ml) and diethyl ether (50 ml). The layers were separated and the aqueous phase extracted with diethyl ether (2×20 ml). The combined organic layers were washed with brine (20 ml), dried over magnesium sulfate, filtered and concentrated in vacuo, to give an oil. Purification via flash column chromatography (SiO2-ethyl acetate/petroleum ether, 1:2, v/v) afforded the title compound (141 mg, 66%) as a pale yellow oil. δH(CD3OD) 1.57-1.70 (2H, m), 2.02-2.25 (2H, m), 2.34-2.49 (2H, m), 2.60 (1H, m), 3.03 (1H, m), 3.24 (1H, m), 3.47 (3H, s), 3.52 (3H, s), 5.17 (2H, s), 5.23(2H, s), 5.33 (1H, s), 6.68 (1H, dd), 6.83 (1H, d), 7.09 (1H, d).

Aufarbeitung

  1. customTo a round bottomed flask equipped
  2. additionThe reaction mixture was poured into a separating funnel
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with diethyl ether (2×20 ml)
  5. washThe combined organic layers were washed with brine (20 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give an oil
  10. customPurification via flash column chromatography (SiO2-ethyl acetate/petroleum ether, 1:2, v/v)

Quellen und Nachweise

ORD-Eintrag
ord-33f25b0cefc44aba9fb9eddfc86a2802
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06797731B2

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