2-(Ethylthio)ethanol → HCID 58903166, Verbindung

HRID 273409

Reaktionsgleichung

Reaktionsgleichung von HRID 273409
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:19][CH:18]=3)[CH:10]=2)=[C:4]([CH3:32])[CH:3]=1.[CH2:33]([S:35][CH2:36][CH2:37]O)[CH3:34].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.C(OCC)C>[CH2:33]([S:35][CH2:36][CH2:37][O:1][C:2]1[CH:3]=[C:4]([CH3:32])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])=[CH:19][CH:18]=3)[CH:10]=2)=[C:6]([CH3:8])[CH:7]=1)[CH3:34]

Komponenten

7

Edukt 4

HCID 80752-(Ethylthio)ethanol2×HCID 13831Tributylphosphine2×HCID 730421,1'-(Azodicarbonyl)dipiperidine2×HCID 58903199Tert-butyl 3-{4-[(4'-hydroxy-2',6'-dimethylbiphenyl-3-yl)methoxy]phenyl}propanoate

Produkt 1

HCID 58903166HCID 58903166, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 3-{4-[(4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methoxy]phenyl}propanoate (1.69 g, 3.91 mmol), 2-(ethylthio)ethanol (0.46 mL, 4.30 mmol) and tributylphosphine (1.46 mL, 5.86 mmol) in tetrahydrofuran (33 mL) was added 1,1′-(azodicarbonyl)dipiperidine (1.48 g, 5.86 mmol) at room temperature with stirring. The reaction mixture was stirred at room temperature for 16 hrs., and an equivalent amount of the aforementioned reagents (2-(ethylthio)ethanol, tributylphosphine and 1,1′-(azodicarbonyl)dipiperidine) were added at the same temperature and the mixture was further stirred for 16 hrs. Diethyl ether was added to the reaction mixture and insoluble material was filtered off. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1) to give the title compound (1.40 g, yield 69%) as a colorless oil.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 16 hrs
  2. stirringthe mixture was further stirred for 16 hrs
  3. filtrationwas filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-33849a60b49c4c0284595f583f7468ed
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456218B2

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