Triethylamine → 3,4-Dihydro-4,4-dimethyl-6-(trimethlsilanyl)ethynylspiro[2H-1-benzopyran-2,1'-cyclopropane]

HRID 1861365Notes

Reaction equation

HRID 1861365 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:12][C:9]3([CH2:11][CH2:10]3)[CH2:8][C:7]([CH3:14])([CH3:13])[C:6]=2[CH:15]=1.C(N(CC)CC)C.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25]>[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.O1CCCC1>[CH3:13][C:7]1([CH3:14])[C:6]2[CH:15]=[C:2]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])[CH:3]=[CH:4][C:5]=2[O:12][C:9]2([CH2:11][CH2:10]2)[CH2:8]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 22568885HCID 22568885, compound2×

Product 1

HCID 225688793,4-Dihydro-4,4-dimethyl-6-(trimethlsilanyl)ethynylspiro[2H-1-benzopyran-2,1'-cyclopropane]

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Following general procedure D and using 6-bromo-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1′-cyclopropane] (Intermediate 36, 0.44 g, 1.65 mmol), triethyl amine (4 mL), anhydrous tetrahydrofuran (5 mL), copper(I)iodide (0.95 g, 0.5 mmol), trimethylsilyl acetylene (1.62 g, 16.5 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.4 g, 0.56 mmol), the title compound was obtained as a brown oil (0.4 g, 86%).

Sources & evidence

ORD record
ord-2b14c2e8239246f593607b970707d359
Source dataset
uspto-grants-2003_03
Patent number
US06531599B2

Reaction notes

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