Diisopropylethylamine → 3-Isopropylbenzofuran

HRID 1362398Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12].C(N(C(C)C)CC)(C)C>C(#N)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:11]([C:10]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH:9]=1)([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 1-iodo-2-(3-methylbut-2-enyloxy)benzene (5 g, 17.3 mmol) in propionitrile (10 mL) and diisopropylethylamine (9 mL, 52 mmol) is degassed with argon for 15 min. To this solution is added palladium acetate (423 mg, 1.73 mmol) and the reaction is heated to 100° C. overnight. The reaction is then cooled to room temperature and passed through a pad of celite, washing the filter cake with ethyl acetate (50 mL). The ethyl acetate and amine base are then removed under vacuum. The crude reaction mixture is then chromatographed using 100% hexanes to yield title compound as a colorless oil in 52% yield (1.3 g): 1H NMR (300 MHz, CDCl3) δ 7.7 (s, 1H), 7.68 (d, J=9.0 Hz, 1H,), 7.55 (d, J=9.0 Hz, 1H), 7.32-7.24 (m, 2H), 3.11-3.07 (m, 1H), 1.32 (2s, 6H).

Workup

temperatureThe reaction is then cooled to room temperature
washwashing the filter cake with ethyl acetate (50 mL)
customThe ethyl acetate and amine base are then removed under vacuum
customThe crude reaction mixture
customis then chromatographed

Sources & evidence

ORD record: ord-20af22a681084ce5a89ec7fc42ba5731
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879872B2

Reaction notes

Loading…