Trimethylsilylacetylene → Methyl-(3-trimethylsilanylethynyl-benzyl)-carbamic acid tert-butyl ester

HRID 2387708

Reaktionsgleichung

[Si:1]([C:5]#[CH:6])([CH3:4])([CH3:3])[CH3:2].Br[C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[CH2:11][N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16]>C(N(CC)CC)C.[Cu]I>[C:15]([O:14][C:13](=[O:19])[N:12]([CH3:20])[CH2:11][C:10]1[CH:9]=[CH:8][CH:23]=[C:22]([C:6]#[C:5][Si:1]([CH3:4])([CH3:3])[CH3:2])[CH:21]=1)([CH3:18])([CH3:17])[CH3:16]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

TMS-Acetylene (2.2 mL, 15.0 mmol) was added dropwise to commercially available tert-butyl 3-bromobenzyl(methyl)carbamate (3.0 g, 10 mmol), CuI (100 mg, 0.5 mmol) and palladium dichlorobistriphenylphosphine (210 mg, 0.3 mmol) in triethylamine (30 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was heated to 70° C. for 12 hrs before cooling to room temperature and evaporating in vacuo. The residue was triturated with diethyl ether (30 mL), filtered and the filtrate evaporated in vacuo and purified by column chromatography (5% ethyl acetate in hexane) to yield A314.1 (3.2 g, 100%) as a brown oil. HPLC YMC S-5 4.6×33 mm (2 min grad): retention time 2.34 min, M+Na+=340.34

Aufarbeitung

temperaturebefore cooling to room temperature
customevaporating in vacuo
customThe residue was triturated with diethyl ether (30 mL)
filtrationfiltered
customthe filtrate evaporated in vacuo
custompurified by column chromatography (5% ethyl acetate in hexane)
customto yield A314.1 (3.2 g, 100%) as a brown oil
custom4.6×33 mm (2 min grad)

Quellen und Nachweise

ORD-Eintrag: ord-013b702c91bc4f508c0d68b0df41921e
Quelldatensatz: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08268855B2

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