Trimethylsilylacetylene → HCID 90349595, compound

HRID 928878Notes

Reaction equation

HRID 928878 reaction equation
I[C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:7])=[CH:4][CH:3]=1.[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20]>C(N(CC)CC)C.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.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:18][Si:19]([C:22]#[C:23][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:7])=[CH:4][CH:3]=1)([CH3:21])[CH3:20]

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 90349596HCID 90349596, compound

Product 1

HCID 90349595HCID 90349595, compoundYield 99.5%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Under a nitrogen atmosphere, heptyl 4-iodobenzoate (2a) (10.1 g, 29.3 mmol) was dissolved in anhydrous triethylamine (50 mL), Pd(PPh3)2Cl2 (0.0820 g, 0.117 mmol), triphenylphosphine (0.126 g, 0.480 mmol), copper (I) iodide (0.135 g, 0.192 mmol), and trimethylsilylacetylene (TMSA) (4.30 mL, 31.7 mmol) were added, and the mixture was stirred at room temperature for 20 hr. The reaction solution was filtered through celite, the solvent was removed under reduced pressure, and the residue was purified by column chromatography (ethyl acetate:hexane=1:30) to give heptyl 4-[(trimethylsilyl)ethynyl]benzoate (3a) (9.23 g, yield 98%) as an oily liquid.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography (ethyl acetate:hexane=1:30)

Sources & evidence

ORD record
ord-0a8c445e00c142b58ca9a545668f52df
Source dataset
uspto-grants-2016_03
Patent number
US09290592B2

Reaction notes

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