Trimethylsilyl triflate → 2-[3-Bromo-4-(cyclopropylmethoxy)phenyl]-2-methyl-1,3-dioxolane

HRID 1423403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1423403
[Br:1][C:2]1[CH:3]=[C:4]([C:13](=[O:15])[CH3:14])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C[Si](C)(C)[O:30][CH2:31][CH2:32]O[Si](C)(C)C>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:13]2([CH3:14])[O:30][CH2:31][CH2:32][O:15]2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1

Komponenten

5

Edukt 3

HCID 65367Trimethylsilyl triflateHCID 818582,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctaneHCID 629080041-[3-Bromo-4-(cyclopropylmethoxy)phenyl]ethanone

Produkt 1

HCID 670330682-[3-Bromo-4-(cyclopropylmethoxy)phenyl]-2-methyl-1,3-dioxolane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1-(3-bromo-4-cyclopropylmethoxy-phenyl)-ethanone from example B.b13 (14.0 g; 52.0 mmol) in dry dichloromethane (250 mL) was cooled in an ice-bath before addition of trimethylsilyl trifluoro-methane sulfonate (0.23 g; 1.04 mmol) and dropwise addition of 1,2-bis-(trimethylsilyloxy)-ethane (13.15 g; 62.4 mmol). The reaction mixture was stirred for two hours, extracted with 1M aqueous NaHCO3 (100 mL) and dried over MgSO4. The crude is purified by column chromatography on silica gel (ethyl acetate/cyclohexane—9:1) to yield the title compound as pale yellow oil.

Aufarbeitung

  1. extractionextracted with 1M aqueous NaHCO3 (100 mL)
  2. dry with materialdried over MgSO4
  3. customThe crude is purified by column chromatography on silica gel (ethyl acetate/cyclohexane—9:1)

Quellen und Nachweise

ORD-Eintrag
ord-d9853be539944d9ab8791e5fcf621eba
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927557B2

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