1-Methoxybuta-1,3-diene → 4-{2-[(e)-2-Methoxyethenyl]-2,3-dihydro-1-benzofuran-5-yl}benzonitrile

HRID 494814

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1I.[CH3:17][O:18][CH:19]=[CH:20][CH:21]=[CH2:22].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(Cl)Cl.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:17][O:18]/[CH:19]=[CH:20]/[CH:21]1[CH2:22][C:3]2[CH:4]=[C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=3)[CH:6]=[CH:7][C:2]=2[O:1]1

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of Example 1A (0.20 g, 0.623 mmol), 1-methoxybutadiene (0.18 g, 2.18 mmol), palladium diacetate (0.007 g, 0.031 mmol), sodium bicarbonate (0.261 g, 3.11 mmol) and tetrabutyl ammonium chloride (0.173 g, 0.623 mmol) was heated at 60° C. in DMF (3 mL) under an atmosphere of nitrogen for 36 hours. The reaction was cooled to 23° C., diluted with CH2Cl2 (50 mL), filtered through Celite. The solution was concentrated under reduce pressure and the residue was purified on silica using CH2Cl2 to give the titled compound (0.95 g, 55%). 1HNMR (CDCl3): 3.05 (m, 1H), 3.40 (m, 1H), 3.60 (s, 3H), 5.00 (m, 1H), 5.22 (m, 1H), 6.72 (d, J=14 Hz, 1H), 6.83 (d, J=7 Hz, 1H), 7.38 (m, 2H), 7.65 (m, 4H); MS (DCI): 278 (M+H+), 295 (M+NH4+).

Workup

filtrationfiltered through Celite
concentrationThe solution was concentrated
customthe residue was purified on silica

Sources & evidence

ORD record: ord-4ff6943717344cc6a31885b631682cf6
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538138B2

Linked notes

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