Triphenylphosphine → HCID 18620468, Verbindung

HRID 1861594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1861594
[OH:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH:5]=[C:4]([CH3:19])[CH:3]=1.[F:20][C:21]([F:27])([F:26])[S:22][CH2:23][CH2:24]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.CCCCC.C(OCC)(=O)C>[CH3:14][N:13]1[C:9]([O:8][C:6]2[CH:5]=[C:4]([CH3:19])[CH:3]=[C:2]([O:1][CH2:24][CH2:23][S:22][C:21]([F:27])([F:26])[F:20])[N:7]=2)=[CH:10][C:11]([C:15]([F:18])([F:17])[F:16])=[N:12]1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 40896982-(Trifluoromethylsulfanyl)ethanolHCID 178429419HCID 178429419, Verbindung

Produkt 1

HCID 18620468HCID 18620468, VerbindungAusbeute 55,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 22335286Ethyl acetate pentaneLösungsmittel

Versuchsvorschrift

A mixture of 1A (0.55 g), 2-(trifluoromethylthio)-ethanol (0.35 g, Example A), triphenylphosphine (0.64 g) and diethyl azodicarboxylate (0.42 g) in dry tetrahydrofuran (5 ml) is stirred for 20 hours at ambient temperature. The reaction mixture is diluted with pentane/ethyl acetate (by volume ration 1/1) and filtered through a bed of silica gel. The filtrate is washed with water. The organic layer is dried with anhydrous magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v) yields 0.45 g of the title compound as an colorless oil.

Aufarbeitung

  1. filtrationfiltered through a bed of silica gel
  2. washThe filtrate is washed with water
  3. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-fad1989119e94b57b3eb3c7f9657511f
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06534447B1

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