Triethylamine → HCID 9949633, compound

HRID 1018114Notes

Reaction equation

HRID 1018114 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:19]([C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[O:27][CH2:26][CH2:25][C:24]2([CH2:32][O:33][CH3:34])[CH3:31])#[CH:20]>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.[Cu]I.CN(C=O)C>[CH3:34][O:33][CH2:32][C:24]1([CH3:31])[C:23]2[C:28](=[CH:29][CH:30]=[C:21]([C:19]#[C:20][C:2]3[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=3)[CH:22]=2)[O:27][CH2:26][CH2:25]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 69273Methyl 4-iodobenzoateHCID 18406080HCID 18406080, compound

Product 1

HCID 9949633HCID 9949633, compound

Reagents, catalysts & solvents 3

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

Procedure

In 11 ml of abs. DMF was successively dissolved 1.061 g (1.25 eq.) of methyl 4-iodo-benzoate, 114 mg (0.05 eq.) of bis (triphenylphosphine)palladium(II) chloride, 74.1 mg (0.12 eq.) of CuI, and 1.13 ml (2.5 eq.) of triethylamine. 701 mg (3.24 mmol) of the above prepared 6-ethynyl-4-methoxymethyl-4-methyl-chroman, dissolved in 2.7 ml of abs. DMF, was added within 1 h via dropping funnel. After 0.25 h, the reaction was quenched by pouring the reaction mixture onto crushed ice/ HCl. Extraction with diethylether, washing the organic phase twice with water, drying it over magnesium sulfate, filtration and evaporation of the solvent yielded after flash chromatography (SiO2, hexane/ ethylacetate 92/8) 630 mg of the title compound as yellowish oil.

Workup

  1. dissolutiondissolved in 2.7 ml of abs
  2. customthe reaction was quenched
  3. additionby pouring the reaction mixture
  4. customonto crushed ice/ HCl
  5. extractionExtraction with diethylether
  6. washwashing the organic phase twice with water
  7. customdrying it
  8. filtrationover magnesium sulfate, filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-c66680ca8010453abe3f4659d3319b17
Source dataset
uspto-grants-2002_11
Patent number
US06479670B1

Reaction notes

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