Triethylamine → HCID 57849320, compound

HRID 736513Notes

Reaction equation

HRID 736513 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:28][CH3:29])([C:13]2[CH:18]=[CH:17][C:16](OS(C(F)(F)F)(=O)=O)=[C:15]([CH3:27])[CH:14]=2)[CH2:11][CH3:12])=[CH:6][C:5]=1[CH3:30].[CH3:32][Si:33]([C:36]#[CH:37])([CH3:35])[CH3:34].C(N(CC)CC)C>CN(C=O)C>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:28][CH3:29])([C:13]2[CH:18]=[CH:17][C:16]([C:37]#[C:36][Si:33]([CH3:35])([CH3:34])[CH3:32])=[C:15]([CH3:27])[CH:14]=2)[CH2:11][CH3:12])=[CH:6][C:5]=1[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 57849346HCID 57849346, compound

Product 1

HCID 57849320HCID 57849320, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-[1-Ethyl-1-(3-methyl-4-trifluoromethanesulfonyloxy-phenyl)-propyl]-2-methyl-benzoic acid methyl ester (11.20 g, 24.43 mmol) in DMF (100 ml) is added trimethylsilylacetylene (6.90 ml, 48.85 mmol), dichlorobis(triphenylphosphine) palladium (1.71 g, 2.44 mmol) and triethylamine (23.84 ml, 171 mmol) and heated to 80° C. overnight. The reaction mixture is concentrated and filtered through a pad of silica gel eluted with 10% EtOAc/Hexanes. The eluent is concentrated and chromatographed (330 g SiO2, 2% EtOAc/Hexanes) to yield the title compound (8.07 g, 81%) as an orange oil.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. filtrationfiltered through a pad of silica gel
  3. washeluted with 10% EtOAc/Hexanes
  4. concentrationThe eluent is concentrated
  5. customchromatographed (330 g SiO2, 2% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-ae1c3d909cba4c55a317f18212f2faac
Source dataset
uspto-grants-2009_09
Patent number
US07595345B2

Reaction notes

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