Trimethylsilylacetylene → Methyl 2-(2-((trimethylsilyl)ethynyl)phenyl)acetate

HRID 1485140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1485140
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:13][Si:14]([C:17]#[C:18][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10])([CH3:16])[CH3:15]

Komponenten

4

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 640185Methyl 2-(2-iodophenyl)acetate

Produkt 1

HCID 59457733Methyl 2-(2-((trimethylsilyl)ethynyl)phenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418476HCID 178418476, VerbindungKatalysator

Versuchsvorschrift

Methyl 2-(2-iodophenyl)acetate (I9) (4.65 g, 16.8 mmol), PdCl2(PPh3)2 (295 mg, 421 μmol) and Cu(I)I (80.0 mg, 421 μmol) were placed into an oven dried reaction flask under nitrogen. (Trimethylsilyl)acetylene (2.80 mL, 20.2 mmol), dry degassed THF (20 mL) and triethylamine (20 mL) were added and the reaction mixture was stirred at room temperature for 16 hours. The volatiles were removed under reduced pressure to give a black residue which was adsorbed onto silica then chromatographed on silica gel (0-5% ethyl acetate/petroleum benzine 40-60° C.) to give the title compound (I10) (4.63 g, 99%) as a light brown liquid; 1H NMR (400 MHz, CDCl3) δ 7.48 (dd, J=7.5, 0.8 Hz, 1H), 7.32-7.14 (m, 3H), 3.84 (s, 2H), 3.71 (s, 3H), 0.26 (s, 9H). LCMS Method C: rt 6.64 min.

Aufarbeitung

  1. customdried
  2. customreaction flask under nitrogen
  3. customdegassed THF (20 mL) and triethylamine (20 mL)
  4. additionwere added
  5. customThe volatiles were removed under reduced pressure
  6. customto give a black residue which
  7. customthen chromatographed on silica gel (0-5% ethyl acetate/petroleum benzine 40-60° C.)

Quellen und Nachweise

ORD-Eintrag
ord-8e4961bb82a74dd2a25bca8dca0d39b7
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09421205B2

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