Phosphoric Acid → HCID 15279438, Verbindung

HRID 865919Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 865919
[CH3:1][C:2](=[CH2:5])[C:3]#[CH:4].C(N(CC)CC)C.[CH3:13][C:14]1([CH3:33])[O:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:23](OS(C(F)(F)F)(=O)=O)[C:17]=2[C:16](=[O:32])[O:15]1.P(=O)(O)(O)O>CN(C)C=O.O>[CH3:13][C:14]1([CH3:33])[O:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:23]([C:4]#[C:3][C:2]([CH3:5])=[CH2:1])[C:17]=2[C:16](=[O:32])[O:15]1

Komponenten

7

Edukt 4

HCID 1004Phosphoric AcidHCID 8471TriethylamineHCID 62323Isopropenylacetylene2×HCID 10892748HCID 10892748, Verbindung

Produkt 1

HCID 15279438HCID 15279438, VerbindungAusbeute 62,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

0.64 g (0.92 mmol) of bistriphenylphosphinepalladium dichloride, 4.4ml (46 mmol) of 3-methyl-3-buten-1-yne and 24ml of triethylamine are added under nitrogen to a solution of 15.0 g (46 mmol) of 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H(1,3)benzodioxin-4-one in 150 ml of dimethylformamide. The mixture is heated at 115° C. for 0.5 h, a further 6.6 ml of 3-methyl-3-buten-1-yne are then added at this temperature in the course of 1 h and the reaction solution is subsequently stirred for 15 min. After cooling, it is poured into 500 ml of water containing phosphoric acid (pH 3) at 0° C. and extracted with methyl tert-butyl ether, and the combined organic phases are carefully washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated. 14 g of a dark oil remain, which is chromatographed on silica gel using n-hexane/ethyl acetate. 7.0 g of colorless crystals are obtained, m.p. 60° C. (cf. Table 1, No. 1.009).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with methyl tert-butyl ether
  3. washthe combined organic phases are carefully washed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customwhich is chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5d1b5699aeca499093c96cd7009b46b5
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05569640

Notizen zur Reaktion

Wird geladen…