Triethylamine → HCID 66981141, compound

HRID 1050476Notes

Reaction equation

HRID 1050476 reaction equation
Br[C:2]1[CH:13]=[CH:12][C:5]2[O:6][CH:7]([C:9](=[O:11])[CH3:10])[O:8][C:4]=2[CH:3]=1.[CH:14]#[C:15][CH2:16][CH2:17][CH3:18].C(N(CC)CC)C.CCCCCCC>C(#N)C.[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:14]([C:2]1[CH:13]=[CH:12][C:5]2[O:6][CH:7]([C:9](=[O:11])[CH3:10])[O:8][C:4]=2[CH:3]=1)#[C:15][CH2:16][CH2:17][CH3:18]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8900HeptaneHCID 123091-PentyneHCID 66981011HCID 66981011, compound

Product 1

HCID 66981141HCID 66981141, compoundYield 99.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13169693Triphenylphosphine palladium dichlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(5-bromobenzo[d][1,3]dioxol-2-yl)ethanone (4.13 g), copper (I) iodide (0.16 g), pent-1-yne (2.32 g), triphenylphosphine palladium chloride (1.19 g) and triethylamine (7 ml) in acetonitrile (40 ml) was stirred overnight at 50° C. Then 100 ml of heptane were added and the organic layer was washed successively with a 2M HCl solution and three times with water, dried over MgSO4 and concentrated. The crude reaction mixture was purified by flash chromatography on silica gel (eluant heptane/ethyl acetate 97/3) to give 3.91 g (22%) of a colorless oil.

Workup

  1. washthe organic layer was washed successively with a 2M HCl solution and three times with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude reaction mixture
  5. customwas purified by flash chromatography on silica gel (eluant heptane/ethyl acetate 97/3)

Sources & evidence

ORD record
ord-a5b7368ccf7344c1941c5d55b10c96e9
Source dataset
uspto-grants-2016_07
Patent number
US09382500B2

Reaction notes

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