Triethylamine → 3-Nitro-5-(2-trimethylsilylvinyl)benzoic acid methyl ester

HRID 383016

Reaktionsgleichung

Reaktionsgleichung von HRID 383016
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6](I)[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH:41]([Si:43]([CH3:46])([CH3:45])[CH3:44])=[CH2:42]>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2].[N+]([O-])([O-])=O.[Ag+]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:5]=[C:6]([CH:42]=[CH:41][Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 79102VinyltrimethylsilaneHCID 7020599Methyl 3-iodo-5-nitrobenzoate

Produkt 1

HCID 543670333-Nitro-5-(2-trimethylsilylvinyl)benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24470Silver NitrateKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 3-iodo-5-nitrobenzoic acid methyl ester (307 mg, 1.0 mmol), Pd(OAc)2 (67 mg, 0.30 mmol), triphenylphosphine (0.032 g, 0.60 mmol), AgNO3 (170 mg, 1.0 mmol), triethylamine (0.167 ml, 1.2 mmol) and vinyltrimethylsilane (0.309 ml, 2.0 mmol) was dissolved in acetonitrile (10 ml) and the solution was heated to 60° C. in a closed vessel for 48 h. The precipitated salts were filtered off and the filtrate was evaporated. The residue was chromatographed on silica gel using a mixture of ethyl acetate and heptane (1:11) as the eluent. Yield: 210 mg (75%).

Aufarbeitung

  1. filtrationThe precipitated salts were filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel using
  4. additiona mixture of ethyl acetate and heptane (1:11) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-50cc083063be40b48dc71ffea5d405d1
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310243B1

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