Triethylamine → 4,4-Dimethyl-6-trimethylsilanyl-ethynyl-1,2,3,4-tetrahydronaphthalene-1-one

HRID 1935767Notes

Reaction equation

[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[C:9](OS(C(F)(F)F)(=O)=O)[CH:10]=2)[C:5](=[O:20])[CH2:4][CH2:3]1.[CH3:22][Si:23](C#C)([CH3:25])[CH3:24].[CH2:28](N(CC)CC)[CH3:29]>O1CCCC1.C(OCC)C.[Cu]I.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>[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Si:23]([CH3:25])([CH3:24])[CH3:22])[CH:10]=2)[C:5](=[O:20])[CH:4]([C:28]#[CH:29])[CH2:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 4,4-dimethyl-6-trifluoromethylsulfonyloxy-1,2,3,4-tetrahydronaphthalene-1-one (Intermediate 11, 0.46 g, 1.43 mmol) in triethyl amine (3 mL) and anhydrous tetrahydrofuran (8 mL) was treated with copper(I)iodide (0.1 g, 0.53 mmol) and sparged with argon for 5 minutes. Trimethylsilyl acetylene (0.85 mL, 6 mmol) was then added followed by dichlorobis(triphenylphosphine)palladium(II) (0.25 g, 0.36 mmol). The resulting reaction mixture was heated at 70° C. for 17 h. It was then cooled to ambient temperature, diluted with diethyl ether and filtered over a bed of celite. The filtrate was evaporated vacuo to an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent to afford the title compound (0.28 g, 72%).

Workup

customsparged with argon for 5 minutes
customThe resulting reaction mixture
temperatureIt was then cooled to ambient temperature
filtrationfiltered over a bed of celite
customThe filtrate was evaporated vacuo to an oil which

Sources & evidence

ORD record: ord-8d86336423a643dbbf1f1a05775d4309
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06387892B1

Reaction notes

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