Triethylamine → (RS)-tert-Butyl-dimethyl-(4-oxiranylmethyl-phenoxy)-silane

HRID 1419930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1419930
[O:1]1[CH2:3][CH:2]1[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(N(CC)CC)C>C(Cl)Cl>[C:15]([Si:12]([CH3:14])([CH3:13])[O:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][CH:2]2[CH2:3][O:1]2)=[CH:6][CH:7]=1)([CH3:18])([CH3:17])[CH3:16]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 53757927(RS)-4-Oxiranylmethyl-phenol

Produkt 1

HCID 54376003(RS)-tert-Butyl-dimethyl-(4-oxiranylmethyl-phenoxy)-silaneAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(RS)-4-Oxiranylmethyl-phenol (1 g, 6.66 mmol) was dissolved in CH2Cl2 (50 ml) and stirred at room temperature in the presence of tert-butyldimethylsilyl chloride (1.3 g, 8.66 mmol), 4-dimethyl-aminopyridine (0.018 g, 0.15 mmol) and triethylamine (1.2 ml, 8.66 mmol). After 22 hours at room temperature, the reaction mixture was washed with H2O (2×100 ml) and the resulting aqueous phases were extracted with CH2Cl2 (100 ml). The combined organic phases were dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexane-ethylacetate 9:1) to provide (RS)-tert-Butyl-dimethyl-(4-oxiranylmethyl-phenoxy)-silane (1.44 g, 82%) as yellow oil, MS: m/e=264 (M+).

Aufarbeitung

  1. washthe reaction mixture was washed with H2O (2×100 ml)
  2. extractionthe resulting aqueous phases were extracted with CH2Cl2 (100 ml)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel (hexane-ethylacetate 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-ba2cfacf52194902ac123bcf09f7faab
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05889026

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