Dimethylformamide → (5-Tert-butyl-2-methyl-phenylethynyl)trimethyl-silane

HRID 1869950Notes

Reaction equation

HRID 1869950 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:19])=[C:9](OS(C(F)(F)F)(=O)=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:27][Si:28]([C:31]#[CH:32])([CH3:30])[CH3:29].CN(C)C=O>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.CCCCCC>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:19])=[C:9]([C:32]#[C:31][Si:28]([CH3:30])([CH3:29])[CH3:27])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 57424250Trifluoro-methanesulfonic acid 5-tert-butyl-2-methyl-phenyl ester2×

Product 1

HCID 69070941(5-Tert-butyl-2-methyl-phenylethynyl)trimethyl-silaneYield 69.6%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolvent

Procedure

Following General Procedure D and using trifluoro-methanesulfonic acid 5-tert-butyl-2-methyl-phenyl ester (Intermediate 108, 0.28 g, 0.94 mmol), triethyl amine (3 mL), trimethylsilyl acetylene (1 mL, 7 mmol), N,N-dimethylformamide (6 mL) and dichlorobis(triphenylphosphine)palladium(II) (0.053 g, 0.076 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using hexane as the eluent, the title compound (0.16 g, 69%) was obtained. 1H NMR (300 MHz, CDCl3): δ 7.44 (d, J=1.7 Hz, 1H), 7.22 (dd, J=8.2, 1.7 Hz, 1H), 7.10 (d, J=8.2 Hz, 1H), 2.39 (s, 3H), 1.28 (s, 9H), 0.26 (s, 9H).

Sources & evidence

ORD record
ord-b8528ffce31641858fa763ef2e57ad8a
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

Loading…