Tributylphosphine → HCID 57791929, Verbindung

HRID 1513102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1513102
[Br:1][C:2]1[CH:3]=[C:4]([CH2:16]O)[CH:5]=[C:6]([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH:7]=1.[CH2:18]([O:20][C:21](=[O:32])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([SH:30])=[CH:26][C:25]=1[CH3:31])[CH3:19].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1.C(OCC)(=O)C.O>[CH2:18]([O:20][C:21](=[O:32])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30][CH2:16][C:4]2[CH:5]=[C:6]([O:8][Si:9]([C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:10])[CH3:11])[CH:7]=[C:2]([Br:1])[CH:3]=2)=[CH:26][C:25]=1[CH3:31])[CH3:19]

Komponenten

8

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 16641178Ethyl (4-mercapto-2-methylphenoxy)acetateHCID 57791917(3-Bromo-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)methanol

Produkt 1

HCID 57791929HCID 57791929, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

[3-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-phenyl]-methanol (6.4 g; 20.17 mmol) and (4-mercapto-2-methyl-phenoxy)-acetic acid ethyl ester (5.02 g; 22.19 mmol) were dissolved in THF (200 mL). Tributylphosphine (8.15 g; 40.34 mmol) and 1,1′-(azodicarbonyl)dipiperidine (10.17 g; 40.34 mmol) were added, and the reaction mixture was stirred for 14 h at room temperature. Water and ethyl acetate were added to the reaction mixture. The phases were separated. The organic phase was washed with water, dried, and evaporated. The crude product was purified by flash chromatography (heptane: dichloromethane (1:1)). Yield: 8 g; 80%. HPLC-MS: m/z: 527.0 (M+1); Rt: 3.10 min.

Aufarbeitung

  1. customThe phases were separated
  2. washThe organic phase was washed with water
  3. customdried
  4. customevaporated
  5. customThe crude product was purified by flash chromatography (heptane: dichloromethane (1:1))

Quellen und Nachweise

ORD-Eintrag
ord-15bcc24882b54a22b63a3d14d78e607f
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217086B2

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