Triethylamine → 6-Trimethylsilanylethynyl-naphthalene-1-carboxylic acid methyl ester

HRID 1094486Notes

Reaction equation

HRID 1094486 reaction equation
[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].CCN(CC)CC.[CH3:14][O:15][C:16]([C:18]1[C:27]2[C:22](=[CH:23][C:24](OS(C(F)(F)F)(=O)=O)=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)=[O:17]>CN(C=O)C.[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>[CH3:14][O:15][C:16]([C:18]1[C:27]2[C:22](=[CH:23][C:24]([C:2]#[C:1][Si:3]([CH3:6])([CH3:5])[CH3:4])=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)=[O:17]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 22622428Methyl 6-(((trifluoromethyl)sulfonyl)oxy)-1-naphthoate

Product 1

HCID 666399086-Trimethylsilanylethynyl-naphthalene-1-carboxylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 15.6 ml (113 mMol) ethynyl-trimethylsilane (Fluka; Buchs/Switzerland) and 15.7 ml (113 mMol) Et3N in 250 ml degassed DMF is added to 34 g (102 mMol) 6-trifluoromethanesulfonyloxy-naphthalene-1-carboxylic acid methyl ester, 1.0 g (5.2 mMol) CuI and 5.0 g (7.1 mMol) Pd(PPh3)2Cl2 in 250 ml of degassed DMF. After 15 h at rt, the mixture is concentrated partially in vacuo at 40° C. and the residue re-dissolved in sat. NaHCO3 solution and EtOAc. The aq. phase is separated off and extracted twice with EtOAc. The organic layer is washed twice with sat. NaHCO3 solution, water/sat. NaHCO3 solution 1:1 and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; hexane/EtOAc 199:1) gives the title compound as an oil: MS: [M+1]+=283; TLC(hexane/EtOAc 19:1): Rf=0.22.

Workup

  1. concentrationthe mixture is concentrated partially in vacuo at 40° C.
  2. dissolutionthe residue re-dissolved in sat. NaHCO3 solution
  3. customThe aq. phase is separated off
  4. extractionextracted twice with EtOAc
  5. washThe organic layer is washed twice with sat. NaHCO3 solution, water/
  6. dry with materialNaHCO3 solution 1:1 and brine, dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b571b113f23c4e0d9f0d941e0d2eb2e6
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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