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

HRID 381055
Notes
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Reaction equation

HRID 381055 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
ParticipantsProcedureSources & evidenceReaction notes

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)
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 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-103bbf15ed5c4a658461578bb3ba37f7
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06303785B1

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes