Triethylamine → HCID 21107166, compound

HRID 1870019Notes

Reaction equation

HRID 1870019 reaction equation
[CH3:1][C:2]1[C:3](OS(C(F)(F)F)(=O)=O)=[CH:4][C:5]2[C:6]([CH3:14])([CH3:13])[CH2:7][CH2:8][C:9](=[O:12])[C:10]=2[CH:11]=1.C(N(CC)CC)C.[CH3:30][Si:31]([C:34]#[CH:35])([CH3:33])[CH3:32].C(OCC)(=O)C>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>[CH3:13][C:6]1([CH3:14])[C:5]2[C:10](=[CH:11][C:2]([CH3:1])=[C:3]([C:35]#[C:34][Si:31]([CH3:33])([CH3:32])[CH3:30])[CH:4]=2)[C:9](=[O:12])[CH2:8][CH2:7]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 57424268HCID 57424268, compound2×

Product 1

HCID 21107166HCID 21107166, compoundYield 93.7%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolvent

Procedure

Following General Procedure D and using trifluoro-methanesulfonic acid 3,8,8-trimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl ester (Intermediate 172, 5.04 g, 15 mmol), triethyl amine (20 mL), copper(I)iodide (0.6 g, 3 mmol), trimethylsilyl acetylene (5.3 mL, 37.5 mmol) and dichlorobis(triphenylphosphine)palladium(II) (2.2 g, 3 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 6% ethyl acetate in hexane as the eluent, the title compound (4 g, 93%) was obtained as a pale yellow solid.

Sources & evidence

ORD record
ord-5b96f2f2cf96497aa32826699ef3c11a
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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