Triphenylphosphine → 3-Cyclohexyl-4-morpholinoethoxychlorobenzene

HRID 24361

Reaktionsgleichung

Reaktionsgleichung von HRID 24361
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:20]1([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2[OH:33])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.O[CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH:20]1([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2[O:33][CH2:35][CH2:36][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 831204-Chloro-2-cyclohexylphenolHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 542202543-Cyclohexyl-4-morpholinoethoxychlorobenzeneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triphenylphosphine (7.47 g, 19.58 mmol) was added to a solution of 2-cyclohexyl-4-chlorophenol (6 g, 28.48 mmol) and 2-hydroxyethylmorpholine (3.5 g, 28.48 mmol) in tetrahydrofuran (50 ml), followed by the dropwise addition of diethylazodicarboxylate (4.5 ml, 28.48 mmol). The mixture stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure and triturated with dichloromethane/hexanes and then washed with more hexanes. Chromatography (silica, 10-20-30% ethyl acetate/hexanes) afforded 8.4 g (95%) of 3-cyclohexyl-4-morpholinoethoxy-chlorobenzene as a yellowish oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customtriturated with dichloromethane/hexanes
  3. washwashed with more hexanes

Quellen und Nachweise

ORD-Eintrag
ord-0587300284a0486c8710401c67d8f9c2
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855730B2

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