Triethylamine → [(3-Bromophenanthren-9-YL)methoxy](tert-butyl)dimethylsilane

HRID 1646051

Reaktionsgleichung

Reaktionsgleichung von HRID 1646051
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[C:7]([CH2:16][OH:17])[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(N(CC)CC)C.CNC1C=CN=CC=1>C(Cl)Cl.C1COCC1.C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[C:7]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 1230984-(Methylamino)pyridineHCID 15159129(3-Bromophenanthren-9-YL)methanol2×

Produkt 1

HCID 15159130[(3-Bromophenanthren-9-YL)methoxy](tert-butyl)dimethylsilaneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-9-(hydroxymethyl) phenanthrene, 4 (5.96 g, 20.8 mmol) and t-butyldimethylsilyl chloride (4.7 g, 31 mmol) in 100 ml of CH2Cl2 and 20 ml of THF was added triethylamine (4.9 ml, 35 mmol) followed by 4-methylaminopyridine (250 mg, 2.05 mmol). After stirring at room temperature for 20 hours, the solution was poured into 300 ml of ethyl ether and washed successively with sat. NH4Cl, sat. NaHCO3, H2O, and brine. Drying (Na2SO4) and evaporation gave a brown solid which was purified by flash chromatography through 400 g of silica gel (1:4 CH2Cl2 -hexane) to yield 7.23 g (87%) of the title compound as a pale yellow solid.

Aufarbeitung

  1. washwashed successively with sat. NH4Cl, sat. NaHCO3, H2O, and brine
  2. customDrying
  3. custom(Na2SO4) and evaporation
  4. customgave a brown solid which
  5. customwas purified by flash chromatography through 400 g of silica gel (1:4 CH2Cl2 -hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c0a31e0468614ef7807c6bdae9d610f6
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05177202

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