Tetrahydrofuran → 3-[1-(4-Triisopropylsilanyloxymethyl-phenyl)-vinyl]-benzonitrile

HRID 1161079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1161079
O1CCC[CH2:2]1.CC(C)([O-])C.[K+].[CH:12]([Si:15]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[O:16][CH2:17][C:18]1[CH:33]=[CH:32][C:21]([C:22]([C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[C:27]#[N:28])=O)=[CH:20][CH:19]=1)([CH3:14])[CH3:13]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH:12]([Si:15]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[O:16][CH2:17][C:18]1[CH:33]=[CH:32][C:21]([C:22]([C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[C:27]#[N:28])=[CH2:2])=[CH:20][CH:19]=1)([CH3:14])[CH3:13]

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 574383603-(4-Triisopropylsilanyloxymethyl-benzoyl)-benzonitrile

Produkt 1

HCID 666996553-[1-(4-Triisopropylsilanyloxymethyl-phenyl)-vinyl]-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of methyltriphenylphosphonium bromide (0.2 g, 0.56 mmol) and tetrahydrofuran (10 mL) is stirred at 0° C. Potassium tert-butoxide (72 mg, 0.64 mmol) is added and the yellow solution is stirred 10 min at room temperature. The solution is cooled to 0° C. and 3-(4-Triisopropylsilanyloxymethyl-benzoyl)-benzonitrile (0.2 g, 0.51 mmol) is added. The resulting orange reaction is stirred 1 hr at room temperature. The reaction is diluted with water and extracted with ethyl acetate (2×50 mL). The extracts are combined, dried on magnesium sulfate, filtered, and concentrated. The residue is purified via silica chromatography eluting with hexanes to 9:1 hexanes:ethyl acetate to give 90 mg, 45%, as a colorless wax. 1H NMR (CDCl3) δ 7.60-7.67 (m, 3H), 7.47 (t, 1H), 7.37-7.40 (m, 2H) 7.27-7.28 (2H), 5.60 (s, 1H), 5.50 (s, 1H), 1.10-1.29 (m, 21H).

Aufarbeitung

  1. stirringthe yellow solution is stirred 10 min at room temperature
  2. temperatureThe solution is cooled to 0° C.
  3. customThe resulting orange reaction
  4. stirringis stirred 1 hr at room temperature
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. customdried on magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified via silica chromatography
  10. washeluting with hexanes to 9:1 hexanes
  11. customethyl acetate to give 90 mg, 45%

Quellen und Nachweise

ORD-Eintrag
ord-e1d042020178473b814df7b1a82f406d
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816523B2

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