Propargyl alcohol → 1-Benzofuran-2-Ylmethanol

HRID 1420564Notes

Reaction equation

HRID 1420564 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH2:9]([OH:12])[C:10]#[CH:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N)CCC>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2].[Cu]I>[OH:12][CH2:9][C:10]1[O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH:11]=1

Participants

8

Reactant 4

HCID 7859Propargyl alcoholHCID 8007ButylamineHCID 107842-IodophenolHCID 11776Triphenylphosphine

Product 1

HCID 27762631-Benzofuran-2-Ylmethanol

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

2-Iodophenol (500 mg, 2.27 mmol), propargyl alcohol (265 μl, 4.54 mmol), Pd(OAc)2, (5.1 mg, 0.03 mmol), triphenylphosphine (12 mg, 0.046 mmol), n-butylamine (450 μL, 4.5 mmol) and CuI (8.6 mg, 0.045 mmol) were combined in 4.5 mL of THF and the mixture was heated at 40° C. under nitrogen for 36 h. The mixture was cooled to room temperature and the solvents were removed in vacuo and the residue purified by SiO2 column chromatography on 100 g of silica gel, eluting with 20% ethyl acetate in hexanes. 2-(Hydroxymethyl)-benzofuran was obtained by concentration of the product containing fractions. [Kudu, N. G.; Pal, M.; Mahanty, J. S.; Dasgupta, F. K. JCS Chem. Com. 1992, 41]

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvents were removed in vacuo
  3. customthe residue purified by SiO2 column chromatography on 100 g of silica gel
  4. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c07c9585f8eb471685ffc93f771050e4
Source dataset
uspto-grants-2000_06
Patent number
US06071916

Reaction notes

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