Diisopropylethylamine → 3-Isopropylbenzofuran

HRID 2097146Notes

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-480f03d801df49ccb45b3dcb31f6f1d8
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450307B2

Reaction notes

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