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Sodium hydride → ((4'-Chlorobiphenyl-2-yl)methylene)-1,4dioxaspiro[4.5]decane

HRID 2406243
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2406243
[H-].[Na+].[I-].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:7][CH:6]=1.[CH2:37]1[O:47][C:40]2([CH2:45][CH2:44][C:43](=O)[CH2:42][CH2:41]2)[O:39][CH2:38]1.OS([O-])(=O)=O.[Na+]>CS(C)=O>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH:17]=[C:38]2[CH2:37][O:47][C:40]3([CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)[O:39]2)=[CH:9][CH:10]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 516919Sodium BisulfateHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 86667196((4'-Chlorobiphenyl-2-yl)methyl)triphenylphosphonium iodide

Produkt 1

HCID 67054337((4'-Chlorobiphenyl-2-yl)methylene)-1,4dioxaspiro[4.5]decaneAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of sodium hydride (60% in mineral oil, 77 mg, 1.92 mmol) in DMSO (5.8 mL) was heated for 1 hour at 80° C. and then cooled to rt. ((4′-Chlorobiphenyl-2-yl)methyl)triphenylphosphonium iodide (1.04 g, 1.76 mmol) was added to the suspension and then, after stirring 10 minutes at room temperature, 1,4-cyclohexanedione monoethylene acetal (0.25 g, 1.60 mmol) was added. The reaction mixture was heated at 80° C. for 3 hours. After standing at rt overnight, the reaction mixture was poured into a saturated solution of NaHSO4 and extracted with EtOAc. The organic layers were combined, washed with brine, dried with Na2SO4, filtered and concentrated. The crude was purified by flash chromatography (silica gel, 0% to 30% EtOAc in heptane) to give ((4′-Chlorobiphenyl-2-yl)methylene)-1,4dioxaspiro[4.5]decane (0.28 g, 52%) as a white solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.12-7.33 (m, 8 H), 5.98 (s, 1 H), 3.92 (s, 4 H), 2.30-2.36 (m, 2 H), 2.22-2.29 (m, 2 H), 1.62-1.71 (m, 2 H), 1.52-1.58 (m, 2 H).

Aufarbeitung

  1. temperaturecooled to rt
  2. temperatureThe reaction mixture was heated at 80° C. for 3 hours
  3. waitAfter standing at rt overnight
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude was purified by flash chromatography (silica gel, 0% to 30% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-f708ae90dd7f4c9d9bd3bbeb83ffd74d
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08809352B2

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