3,3-Dimethyl-1-butyne → HCID 22647747, compound

HRID 2102884Notes

Reaction equation

HRID 2102884 reaction equation
C[O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1.C(N(CC)C(C)C)(C)C.[CH3:21][C:22]([CH3:26])([CH3:25])[C:23]#[CH:24]>O1CCOCC1.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)I>[CH3:21][C:22]([CH3:26])([CH3:25])[C:23]#[C:24][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:11])=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 135123,3-Dimethyl-1-butyneHCID 69273Methyl 4-iodobenzoateHCID 81531Diisopropylethylamine

Product 1

HCID 22647747HCID 22647747, compoundYield 54.6%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

4-iodobenzoic acid methyl ester (500 mg; 1.9 mmol) was suspended in 1,4-dioxane (3 mL) in a 5 mL reaction vial. To the vessel was added dichlorobis(triphenylphosphine)palladium(II) (44 mg; 3 mol %), copper iodide (7.5 mg), N,N-diisopropylethylamine (0.39 mL; 3.5 mmol) and 3,3-dimethylbut-1-yne (0.275 mL; 3.5 mmol). The vessel was sealed and the mixture was heated at 80° C. for 24 hrs. The solvents were evaporated to dryness and 20 mL of tetrahydrofuran and 20 mL of 10N NaOH was added. The mixture was stirred at room temperature for 30 minutes and the solvent was evaporated. The basic layer was acidified with concentrated HCl and extracted three times with EtOAc. The organic layers were washed with brine and dried over Na2SO4, filtered and evaporated to give the desired product as a brown powder (210 mg; 28%). m/z=203 (M+1).

Workup

  1. customThe vessel was sealed
  2. customThe solvents were evaporated to dryness and 20 mL of tetrahydrofuran and 20 mL of 10N NaOH
  3. additionwas added
  4. customthe solvent was evaporated
  5. extractionextracted three times with EtOAc
  6. washThe organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-9dbbbcdaee7542b997d65539994ff7b0
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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