Imidazole → ((4-Bromothiophen-2-yl)methoxy)(tert-butyl)diphenylsilane

HRID 1363259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1363259
[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][OH:8])[S:5][CH:6]=1.[Si:9](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CN=C1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][O:8][Si:9]([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 2795484(4-Bromo-2-thienyl)methanol

Produkt 1

HCID 59648532((4-Bromothiophen-2-yl)methoxy)(tert-butyl)diphenylsilaneAusbeute 101,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 250-mL round bottom flask fitted with a magnetic stir bar under a N2 atmosphere was added (4-bromothiophen-2-yl)methanol (2.0 g, 10 mmol, 1 equiv) and 30 mL of anhydrous DCM. The reaction mixture was then cooled to 0° C. and the tert-butyl-diphenylsilyl chloride (3.4 g, 3.2 mL, 12.4 mmol, 1.2 equiv) was added followed by imidazole (1.06 g, 15.5 mmol, 1.5 equiv). The reaction was stirred for 16 h and was allowed to equilibrate to rt. The reaction mixture was subsequently taken up in 75 mL DCM and washed with water (100 mL). The organic layer was then dried (Na2SO4), filtered, and evaporated in vacuo. The resulting residue was chromatographed over silica gel (0-10% EtOAc in heptane over 18 min.-retention time (tR) of product: 4-12 min) to give the desired ((4-bromothiophen-2-yl)methoxy)-tert-butyl diphenyl silane (4.3929 g, 98%). 1H-NMR (400 MHz, CD3CN) δ ppm 7.66-7.71 (m, 4H), 7.39-7.51 (m, 6H), 7.29 (d, J=1.46 Hz, 1H), 6.77-6.81 (m, 1H), 4.89 (d, J=0.93 Hz, 2H), 1.06 (s, 9H).

Aufarbeitung

  1. customTo a 250-mL round bottom flask fitted with a magnetic stir bar under a N2 atmosphere
  2. customto equilibrate to rt
  3. washwashed with water (100 mL)
  4. dry with materialThe organic layer was then dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe resulting residue was chromatographed over silica gel (0-10% EtOAc in heptane over 18 min.-retention time (tR) of product: 4-12 min)

Quellen und Nachweise

ORD-Eintrag
ord-8118d00722aa45c5b1eab7ae6c18cf05
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884124B2

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