Acetic Acid → 3-(Benzo[b]thiophen-3-yl)-2-oxopropyl Acetate
Reaction equation
[C:1]([O:4]CC(=O)CC1C=CC(Cl)=C(Cl)C=1)(=[O:3])[CH3:2].[S:17]1[CH:21]=[C:20]([CH2:22][C:23](=[O:26])[CH2:24]Cl)[C:19]2[CH:27]=[CH:28][CH:29]=[CH:30][C:18]1=2.C(O)(=O)C.C(N(CC)CC)C>>[C:1]([O:4][CH2:24][C:23](=[O:26])[CH2:22][C:20]1[C:19]2[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=2[S:17][CH:21]=1)(=[O:3])[CH3:2]Participants
5
Procedure
The procedure described above for the synthesis of 3-(3,4-dichlorophenyl)-2-oxopropyl acetate was followed, reacting 1-(benzo[b]thiophen-3-yl)-3-chloropropan-2-one (0.661 g, 2.94 mmol) with acetic acid (0.34 mL, 0.35 g, 5.9 mmol) and triethylamine (0.82 mL, 0.59 g, 5.9 mmol). Flash chromatography over silica gel (10-40% ethyl acetate in hexanes) gave pure product (0.372 g, 51% yield): 1H NMR (400 MHz, CDCl3) δ 2.14 (s, 3H) 3.98 (s, 2H) 4.71 (s, 2H) 7.34-7.44 (m, 3H) 7.67-7.70 (m, 1H) 7.86-7.89 (m, 1H).
Sources & evidence
- ORD record
- ord-d55c715090c14942861801e3160916e6
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07465798B2
Reaction notes
Loading…