Water → 4-(4-Methoxy-3-methylphenyl)but-3-yn-1-ol

HRID 2220167Notes

Reaction equation

HRID 2220167 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([CH3:8])[CH:7]=1.[CH2:11]([OH:15])[CH2:12][C:13]#[CH:14].C(N(CC)CC)C.O>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>[CH3:10][O:9][C:5]1[CH:4]=[CH:3][C:2]([C:14]#[C:13][CH2:12][CH2:11][OH:15])=[CH:7][C:6]=1[CH3:8]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 135663-Butyn-1-OLHCID 6083154-Bromo-1-methoxy-2-methylbenzene

Product 1

HCID 607996814-(4-Methoxy-3-methylphenyl)but-3-yn-1-olYield 34.3%

Reagents, catalysts & solvents 3

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

Procedure

A stirred solution of 4.6 grams (0.023 mole) of 5-bromo-2-methoxytoluene (commercially available), 3 mL (0.040 mole) of 3-butyn-1-ol, 0.30 gram (0.002 mole) of copper(I) iodide, 14 mL (0.100 mole) of triethylamine, and 0.25 gram (0.0004 mole) of dichlorobis(triphenylphosphine)palladium(II) in 60 mL of DMF was heated at 90° C. for about 18 hours. After this time, the reaction mixture was poured into water and extracted with diethyl ether. The ether extract was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel using mixtures of hexane and ethyl acetate as an eluant. The appropriate fractions of eluate were combined and concentrated under reduced pressure, yielding 1.5 grams of subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe ether extract
  3. dry with materialwas dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a residue
  6. customThe residue was purified by column chromatography on silica gel using mixtures of hexane and ethyl acetate as an eluant
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b729511af44d4bffaf498c38b312bb93
Source dataset
uspto-grants-2008_08
Patent number
US07417057B2

Reaction notes

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