Dimethylformamide → 8-Ethyl-4,4-dimethyl-6-(trimethylsilanyl)ethynyl-3,4-dihydro-2H-naphthalen-1-one

HRID 2377504Notes

Reaction equation

HRID 2377504 reaction equation
[CH2:1]([C:3]1[C:12]2[C:11](=[O:13])[CH2:10][CH2:9][C:8]([CH3:15])([CH3:14])[C:7]=2[CH:6]=[C:5](OS(C(F)(F)F)(=O)=O)[CH:4]=1)[CH3:2].C(N(CC)CC)C.CN(C)C=O.[CH3:36][Si:37]([C:40]#[CH:41])([CH3:39])[CH3:38]>CCCCCC.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>[CH2:1]([C:3]1[CH:4]=[C:5]([C:41]#[C:40][Si:37]([CH3:39])([CH3:38])[CH3:36])[CH:6]=[C:7]2[C:12]=1[C:11](=[O:13])[CH2:10][CH2:9][C:8]2([CH3:15])[CH3:14])[CH3:2]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 86600197Trifluoro-methanesulfonic acid 4-ethyl-8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2yl ester2×

Product 1

HCID 211072528-Ethyl-4,4-dimethyl-6-(trimethylsilanyl)ethynyl-3,4-dihydro-2H-naphthalen-1-oneYield 106.9%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following General Procedure D and using trifluoro-methanesulfonic acid 4-ethyl-8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2yl ester (Intermediate 178, 0.9 g, 2.57 mmol), triethyl amine (6 mL), anhydrous N,N-dimethylformamide (5 mL), dichlorobis(triphenylphosphine)palladium(II) (0.144 g, 0.2 mmol) and (trimethylsilyl)acetylene (2 mL, 13.64 mmol), the reaction was conducted overnight in a sealed tube at 90° C. Work-up followed by flash column chromatography over silica gel (230-400 mesh) using 2-3% ethyl acetate in hexane as the eluent to afforded the title compound as an orange oil (0.82 g, quantitative).

Sources & evidence

ORD record
ord-6250f84c024942c3824035a014d04a92
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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