3,3-Dimethyl-1-butyne → HCID 57804220, compound

HRID 2102916Notes

Reaction equation

HRID 2102916 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[CH3:14][C:15]([CH3:19])([CH3:18])[C:16]#[CH:17]>CCN(CC)CC.[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>[CH3:13][O:12][C:4]1[CH:3]=[C:2]([C:17]#[C:16][C:15]([CH3:19])([CH3:18])[CH3:14])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 2

HCID 135123,3-Dimethyl-1-butyneHCID 15128242Methyl 4-bromo-2-methoxybenzoate

Product 1

HCID 57804220HCID 57804220, compoundYield 91.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 4-bromo-2-methoxybenzoate (1.2 g, 0.0049 mol), copper(I) iodide (0.093 g, 0.00049 mol), 3,3-dimethyl-1-butyne (0.70 mL, 0.0059 mol) and bis(triphenylphosphine)palladium(II) chloride (0.34 g, 0.00049 mol) in Et3N (10 mL) was heated at 100° C. in a 50 mL sealed reaction vessel for 16 hours. After cooling, the mixture was filtered through Celite® and the filter cake was washed repeatedly with ethyl acetate. The filtrate was concentrated under vacuum and the residue was purified by column chromatography on silica gel to give a viscous oil (1.10 g, 91%).

Workup

  1. customsealed
  2. customreaction vessel for 16 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite®
  5. washthe filter cake was washed repeatedly with ethyl acetate
  6. concentrationThe filtrate was concentrated under vacuum
  7. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6873cdab8e4145bbaea831c60fe7619d
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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