Triethylamine → (Z)-tert-Butyl(1-(3-bromophenyl)prop-1-enyloxy)dimethylsilane

HRID 1399540

Reaktionsgleichung

Reaktionsgleichung von HRID 1399540
[C:1]([Si:5]([O:8]/[C:9](/[C:12]1[CH:17]=[CH:16][CH:15]=[C:14](Cl)[CH:13]=1)=[CH:10]\[CH3:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[Br:19]CCC(C1C=CC=CC=1)=O.[Si](OS(C(F)(F)F)(=O)=O)(C(C)(C)C)(C)C.CCN(CC)CC>C(Cl)Cl>[C:1]([Si:5]([O:8]/[C:9](/[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Br:19])[CH:13]=1)=[CH:10]\[CH3:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 1224323-Bromo-1-phenylpropan-1-oneHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 113005611-Chloro-3-[(1Z)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-propen-1-yl]-benzene

Produkt 1

HCID 46838064(Z)-tert-Butyl(1-(3-bromophenyl)prop-1-enyloxy)dimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Compound 9d was synthesized by a procedure similar to that described for 9a using commercially available 3-bromopropiophenone (8d, 1.0 g, 0.0047 mol), TBDMSOTf (1.4 mL, 5.1 mmol), and Et3N (1.1 mL) in CH2Cl2 (10 mL). After workup, 1.15 g (75%) of crude 9d was isolated as colorless oil with a Z-E ratio of 94:6: 1H NMR (CDCl3) δ 7.64-7.58 (m, 1H), 7.41-7.34 (m, 2H), 7.17 (t, 1H, J=8.04 Hz), 5.25 (q, 1H, J=6.9 Hz), 1.75 (d, 3H, J=6.9 Hz), 1.02 (s, 9H), −0.03 (s, 6H); 13C NMR (CDCl3) δ 148.8, 141.9, 130.2, 129.5, 128.7, 124.1, 122.1, 25.8, 18.3, 11.8, −4.0. C15H23BrOSi.

Aufarbeitung

  1. customCompound 9d was synthesized by a procedure similar to

Quellen und Nachweise

ORD-Eintrag
ord-cbaa3db6f644490daef47eedf7d89873
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906908B2

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