3-Butyn-1-OL → methyl 4-(4-hydroxy-1-butynyl)phenylacetate

HRID 2289116Notes

Reaction equation

HRID 2289116 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH2:13]([OH:17])[CH2:14][C:15]#[CH:16]>C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[OH:17][CH2:13][CH2:14][C:15]#[C:16][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 135663-Butyn-1-OLHCID 316783Methyl 2-(4-bromophenyl)acetate

Product 1

HCID 10536788methyl 4-(4-hydroxy-1-butynyl)phenylacetateYield 80.2%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of methyl 4-bromophenylacetate (229 mg, 1.0 mmole) and 3-butyn-1-ol (151 μL, 2.0 mmole) in triethylamine (4.0 mL) was added cuprous bromide (18 mg, 0.12 mmole) and tetra(triphenylphosphine)palladium (46 mg, 0.04 mmole), and the mixture refluxed under a nitrogen atmosphere for 1 hr 20 min. The mixture was evaporated in vacuo and the residue partitioned with water and ether. The organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuo to an oil. Flash chromatography on silica gel in 7:3 hexane:ethyl acetate afforded the title compound (175 mg) as an oil NMR (CDCl3): δ 1.69 (s, 1H); 2.71 (t, 2H); 3.63 (s, 2H); 3.71 (s, 3H); 3.83 (t, 2H); 7.22 (d, 2H); 7.38 (d, 2H).

Workup

  1. temperaturethe mixture refluxed under a nitrogen atmosphere for 1 hr 20 min
  2. customThe mixture was evaporated in vacuo
  3. customthe residue partitioned with water and ether
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo to an oil

Sources & evidence

ORD record
ord-eb9283eec26846b5bd844bcd62f0b1fe
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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