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

HRID 705730

Reaktionsgleichung

Reaktionsgleichung von HRID 705730
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-0044ed38940e4821936da90aa8ee8ab2
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174946B2

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