1,3-Dichlorobenzene → 3-Methyl-4-allyloxy-7-(2-thienoyl)benzofuran

HRID 1084859Notes

Reaction equation

HRID 1084859 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:18][CH2:19][CH:20]=[CH2:21])=[CH:8][CH:9]=[C:10]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])[C:5]=2[O:4][CH:3]=1.Cl[C:23]1[CH:28]=CC=C(Cl)[CH:24]=1>>[CH3:1][C:2]1[C:6]2[C:7]([OH:18])=[C:8]([CH2:28][CH:23]=[CH2:24])[CH:9]=[C:10]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])[C:5]=2[O:4][CH:3]=1.[CH3:1][C:2]1[C:6]2[C:7]([O:18][CH2:19][CH:20]=[CH2:21])=[CH:8][CH:9]=[C:10]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])[C:5]=2[O:4][CH:3]=1

Participants

4

Reactant 2

HCID 109431,3-DichlorobenzeneHCID 151240043-Methyl-4-allyloxy-7-(2-thienoyl)benzofuran

Product 2

HCID 151240043-Methyl-4-allyloxy-7-(2-thienoyl)benzofuranHCID 151240053-Methyl-4-hydroxy-5-(2-propen-1-yl)-7-(2-thienoyl)benzofuran

Procedure

A solution of 3-methyl-4-allyloxy-7-(2-thienoyl)benzofuran (0.43 g, 1.44 mmol) in 1,3-dichlorobenzene (4 mL) was heated to reflux under nitrogen for five hours. The reaction mixture was cooled and the product purified by preparative HPLC, using 10% ethyl acetate in hexane as eluant, to afford 3-methyl-4-hydroxy-5-(2-propen-1-yl)-7-(2-thienoyl)benzofuran, compound 4. An analytical sample was obtained by recrystallization from ether/hexane. 1H NMR d 2.43 (3H, d, J=2 Hz), 3.54 (2H, d, J=6 Hz), 5.30 (2H, m), 5.86 (1H, s), 6.10 (1H, m), 7.16 (1H, dd, J=4 Hz, 4 Hz), 7.34 (1H, d, J=2 Hz), 7.50 (1H, s), 7.65 (1H, d, J=4 Hz), 7.72 (1H, d, J=4 Hz).

Workup

  1. temperatureto reflux under nitrogen for five hours
  2. temperatureThe reaction mixture was cooled
  3. customthe product purified by preparative HPLC

Sources & evidence

ORD record
ord-c111a477a50f4d59886866afb30eb1c0
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

Loading…