Triethylamine → HCID 21107124, compound

HRID 1870036Notes

Reaction equation

HRID 1870036 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[CH:8]=[C:7](OS(C(F)(F)F)(=O)=O)[CH:6]=[CH:5][C:4]=2[C:3]1=[O:22].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>[CH3:1][CH:2]1[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:35]#[C:34][Si:31]([CH3:33])([CH3:32])[CH3:30])[CH:8]=2)[C:3]1=[O:22]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 57424270HCID 57424270, compound2×

Product 1

HCID 21107124HCID 21107124, compoundYield 104.6%

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 6,8,8-trimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl ester (Intermediate 196, 1.45 g, 4.3 mmol), triethyl amine (5 mL), copper(I)iodide (0.21 g, 0.26 mmol), trimethylsilyl acetylene (3 mL, 21 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.75 g, 1.07 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent, the title compound (1.28 g, ˜100%) was obtained.

Sources & evidence

ORD record
ord-2de3cb95e6144c19a32b011e483e9a2f
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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