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Tetrahydrofuran → HCID 89648652, Verbindung

HRID 1774010
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1774010
[H-].[Na+].P(=O)([O-])O[C:5]([CH3:17])(C)[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[C:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)(=O)[CH3:21].[CH2:29]1COCC1>>[CH2:9]([O:8][C:6](=[O:7])/[CH:5]=[C:17](/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)\[CH3:29])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1.[CH2:9]([O:8][C:6](=[O:7])/[CH:21]=[C:20](\[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)/[CH3:29])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 142862-AcetylpyridineHCID 24758Sodium hydrideHCID 178460563HCID 178460563, Verbindung

Produkt 2

HCID 89648652HCID 89648652, VerbindungHCID 89648653HCID 89648653, Verbindung

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of sodium hydride 60% dispersion in mineral oil (480 mg, 12 mmol, 1.2 eq.) in THF (20 mL) at 0° C., dimethyl(benzyloxycarbonyl)methyl phosphonate (2.14 ml, 10 mmol, 1.0 eq.) was added dropwise. The mixture was stirred at 0° C. for 15 min. 2-Acetyl pyridine (1.14 mL, 10 mmol, 1.0 eq.) was added dropwise. The mixture was slowly warmed up to r.t. and stirred at r.t. for 18 hours (the ice bath was let expire). The reaction mixture was quenched with sat. aq. NaHCO3 soln. (50 mL). The mixture was extracted with DCM (3×50 mL). The comb. org. phases were washed with sat. aq. NaCl soln., dried over MgSO4, and concentrated in vacuo. The residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 40 fractions of 45 mL, Heptane 100% to Heptane+40% AcOEt) to yield (E)-3-pyridin-2-yl-but-2-enoic acid benzyl ester as a white solid (LC-MS 3: tR=0.84 min; 254.3) and (Z)-3-pyridin-2-yl-but-2-enoic acid benzyl ester (LC-MS 3: tR=0.63 min; 254.3) as a colorless oil (E/Z ratio ca. 55:13).

Aufarbeitung

  1. temperatureThe mixture was slowly warmed up to r.t.
  2. customThe reaction mixture was quenched with sat. aq. NaHCO3 soln
  3. extractionThe mixture was extracted with DCM (3×50 mL)
  4. washphases were washed with sat. aq. NaCl soln
  5. dry with material, dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 40 fractions of 45 mL, Heptane 100% to Heptane+40% AcOEt)

Quellen und Nachweise

ORD-Eintrag
ord-18f0a7428bb84da7ae93dbe3eeaeb6a4
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09255090B2

Notizen zur Reaktion

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