Triethylamine → {3-[3-(2-Methoxy-ethyl)-cyclobutyl]-phenylethynyl}-triisopropyl-silane

HRID 2240966Notes

Reaction equation

HRID 2240966 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[CH2:11][CH:10]([CH2:12][CH2:13][O:14][CH3:15])[CH2:9]2)[CH:3]=1.[CH:16]([Si:19]([C:26]#[CH:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])([CH3:18])[CH3:17].C(N(CC)CC)C>[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][O:14][CH2:13][CH2:12][CH:10]1[CH2:11][CH:8]([C:4]2[CH:3]=[C:2]([C:27]#[C:26][Si:19]([CH:16]([CH3:18])[CH3:17])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[CH:7]=[CH:6][CH:5]=2)[CH2:9]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734682(Triisopropylsilyl)acetyleneHCID 593053151-Bromo-3-[3-(2-methoxy-ethyl)-cyclobutyl]-benzene

Product 1

HCID 59305302{3-[3-(2-Methoxy-ethyl)-cyclobutyl]-phenylethynyl}-triisopropyl-silaneYield 90.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

In a CEM snap top microwave vial were combined 1-Bromo-3-[3-(2-methoxy-ethyl)-cyclobutyl]-benzene (0.340 gm 1.28 mmol), triisopropylsilylacetylene (0.29 g, 1.12 mmol), copper iodide (9 mg, 0.178 mmol), tetrakis(triphenylphosphine)palladium (29 mg, 0.088 mmol) and triethylamine (1.30 g, 12.8 mmol). The vial was quickly agitated then irradiated in a CEM Explorer™ microwave instrument for 30 minutes at 80° C. Purification by column chromatography (hexanes) afforded an oil 375 mg (80%). This material was used in next step without further characterization.

Workup

  1. customthen irradiated in a CEM Explorer™ microwave instrument for 30 minutes at 80° C
  2. customPurification by column chromatography (hexanes)

Sources & evidence

ORD record
ord-6172c194434a46a2974d92dffd81535c
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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