Tributylamine → 3-Methyl-5-isopropylbenzofuran

HRID 589672

Reaction equation

HRID 589672 reaction equation
C(C1C(I)=[C:6]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[C:16](CC=C)[C:15]=2I)[CH:7]=[CH:8]C=1C(C)C)C=C.N(CCCC)(CCCC)CCCC.C([O-])=O.[NH4+]>C([N+]1C=CN(C)C=1)CCC.F[B-](F)(F)F.Cl[Pd]Cl>[CH:20]([C:17]1[CH:18]=[CH:19][C:14]2[O:13][CH:6]=[C:7]([CH3:8])[C:15]=2[CH:16]=1)([CH3:21])[CH3:22]

Participants

6

Reactant 3

HCID 7622TributylamineHCID 2723923Ammonium formateHCID 66799798HCID 66799798, compound

Product 1

HCID 148135433-Methyl-5-isopropylbenzofuranYield 127.5%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalyst2×HCID 27341781-Butyl-3-methylimidazolium tetrafluoroborateSolvent

Conditions

Temperature
60 °C

Procedure

According to the method described by Xie et al. (Xie et al., (2004) Tetrahedron Lett. 45, 6235-6237) a mixture of allyl-2-iodo-4-isopropylphenyl ether (300 mg, 0.99 mmol), NBu3 (350 μL, 1.49 mmol), ammonium formate (65 mg, 1.03 mmol) and PdCl2 (10 mg, 0.06 mmol) in 1-butyl-3-methylimidazolium-tetrafluoroborate (1.5 mL) was heated at 60° C. for 2 days. A second portion of PdCl2 (24 mg) was added and the mixture was heated at 60° C. additional 5 h. The reaction mixture was extracted with Et2O. Evaporation of the solvent afforded 220 mg crude product, which was purified on silica giving the title compound in 30% yield (55 mg). 1H NMR (400 MHz, CDCl3) δ ppm 1.31 (d, J=6.90 Hz, 6 H) 2.24 (d, J=1.25 Hz, 3 H) 3.03 (spt, J=6.90 Hz, 1 H) 7.17 (dd, J=8.34, 1.94 Hz, 1 H) 7.34-7.39 (m, 3 H).

Workup

  1. temperaturethe mixture was heated at 60° C. additional 5 h
  2. extractionThe reaction mixture was extracted with Et2O
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b66f0b9d3c8c4d5280038664c72e634d
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Linked notes

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