2-Methyl-3-butyn-2-ol → HCID 22112194, compound

HRID 564669Notes

Reaction equation

HRID 564669 reaction equation
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[CH3:9].[CH3:10][C:11]([OH:15])([CH3:14])[C:12]#[CH:13]>[Pd].C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu](I)I.C(NCC)C>[F:1][C:2]1[CH:7]=[C:6]([C:13]#[C:12][C:11]([CH3:14])([OH:15])[CH3:10])[CH:5]=[CH:4][C:3]=1[CH3:9]

Participants

6

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 1234922-Fluoro-4-iodotoluene

Product 1

HCID 22112194HCID 22112194, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 11980388HCID 11980388, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

The mixture of 2-fluoro-4-iodotoluene (0.05 mol), 3-methyl-3-hydroxy-1-butyne (0.06 mol), tetrakis (triphenylphosphonium) palladium (0) 0.35 g, copper iodide 50 mg, and diethylamine 100 ml was refluxed for 5.5 hours. Diethylamine was distilled away under reduced pressure, the residue was extracted with diethylether, and the extract was washed with water. From the extract, diethylether was distilled away, the residue was purified by column chromatography (elution liquid: heptane-ethyl acetate) to obtain colorless oily 2-fluoro-4-(3-methyl-3-hydroxy-1-butynyl)toluene (0.035 mol).

Workup

  1. temperaturewas refluxed for 5.5 hours
  2. distillationDiethylamine was distilled away under reduced pressure
  3. extractionthe residue was extracted with diethylether
  4. washthe extract was washed with water
  5. distillationFrom the extract, diethylether was distilled away
  6. customthe residue was purified by column chromatography (elution liquid: heptane-ethyl acetate)

Sources & evidence

ORD record
ord-f1b52e810b6d4133a21517e0498647eb
Source dataset
uspto-grants-2001_01
Patent number
US06168728A

Reaction notes

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