3-Butyn-1-OL → 3-(4-Hydroxybut-1-ynyl)phenyl acetate

HRID 916837Notes

Reaction equation

HRID 916837 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7](I)[CH:6]=1)(=[O:3])[CH3:2].[CH2:12]([OH:16])[CH2:13][C:14]#[CH:15]>C(#N)C.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>[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:15]#[C:14][CH2:13][CH2:12][OH:16])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 135663-Butyn-1-OLHCID 131017693-Iodophenyl acetate

Product 1

HCID 693863133-(4-Hydroxybut-1-ynyl)phenyl acetate

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 3-iodophenyl acetate (5.6 g) (J. Org. Chem. 1983, 48,1542-4) in acetonitrile (100 mL) was treated with (Ph3P)2PdCl2 (673 mg) and Cul (368 mg) and stirred at room temperature. 3-Butyn-1-ol (1.78 g) was added and the reaction mixture stirred for a further 20 h and concentrated in vacuo. The residue was purified by chromatography (SPE, gradient from cyclohexane to DCM) to give the title compound. LCMS RT=2.54 min

Workup

  1. stirringthe reaction mixture stirred for a further 20 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography (SPE, gradient from cyclohexane to DCM)

Sources & evidence

ORD record
ord-5915486f259d426296cf00db2c3c84e6
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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