Tetrahydrofuran → 8-Cyclopropyl-4,4-dimethyl-6-(trimethylsilanyl)ethynyl-1-tetralone

HRID 2377485Notes

Reaction equation

HRID 2377485 reaction equation
[CH:1]1([C:4]2[C:13]3[C:12](=[O:14])[CH2:11][CH2:10][C:9]([CH3:16])([CH3:15])[C:8]=3[CH:7]=[C:6](OS(C(F)(F)F)(=O)=O)[CH:5]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.O1CCCC1.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39]>CCCCCC.[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.C(OCC)(=O)C>[CH:1]1([C:4]2[CH:5]=[C:6]([C:42]#[C:41][Si:38]([CH3:40])([CH3:39])[CH3:37])[CH:7]=[C:8]3[C:13]=2[C:12](=[O:14])[CH2:11][CH2:10][C:9]3([CH3:16])[CH3:15])[CH2:3][CH2:2]1

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 86600196Trifluoro-methanesulfonic acid 4-cyclopropyl-8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl ester2×

Product 1

HCID 211072428-Cyclopropyl-4,4-dimethyl-6-(trimethylsilanyl)ethynyl-1-tetralone

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following General Procedure B and using trifluoro-methanesulfonic acid 4-cyclopropyl-8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2yl ester (Intermediate 158, 1.09 g, 3 mmol), triethyl amine (5 mL), tetrahydrofuran (5 mL), copper(I)iodide (0.12 g, 0.6 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.42 g, 0.6 mmol) and (trimethylsilyl)acetylene (2.2 mL, 15 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 7% ethyl acetate in hexane as the eluent, the title compound was obtained as an orange oil (1.05 g, quantitative).

Sources & evidence

ORD record
ord-8a896c822b264e2191769c208ae263b0
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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