Sodium Carbonate → 3-Propyl-benzofuran

To a solution of 1-but-2-enyloxy-iodobenzene (4.00 g, 13.8 mmol) in DMF (46 mL) was added n-Bu4NCl (5.36 g. 19.3 mmol), Pd(OAc)2 (0.168 g, 0.690 mmol), Na2CO3 (2.99 g, 28.2 mmol) and NaOAc (1.13 g, 13.8 mmol). The mixture was heated to reflux under nitrogen atmosphere overnight. The mixture was diluted with EtOAc and washed with water. The aqueous layer was extracted with EtOAc (3×). The combined organics were washed with brine and dried over Na2SO4. Purification by column chromatography (silica gel, hexanes) gave the title compound (1.79 g, 81%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.75 (s, 1H), 7.63-7.60 (m, 1H), 7.54 (d, J=7.5 Hz, 1H), 7.33-7.22 (m, 2H), 2.64-2.59 (m, 2H), 1.72-1.64 (m, 2H), 0.96 (t, J=7.2 Hz, 3H); ESI MS m/z 161 (M+H)+.

1. temperatureThe mixture was heated
2. temperatureto reflux under nitrogen atmosphere overnight
3. washwashed with water
4. extractionThe aqueous layer was extracted with EtOAc (3×)
5. washThe combined organics were washed with brine
6. dry with materialdried over Na2SO4
7. customPurification by column chromatography (silica gel, hexanes)

ORD record

ord-4a3dc06054d34406920f01e40ab0bb3f

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450307B2