HCID 57971674, compound → HCID 57971713, compound
Reaction equation
[CH2:1]([O:5][CH:6]([O:8][NH:9][C:10]([C:12]1[S:16][C:15]2[CH:17]=[C:18]([CH2:21][OH:22])[CH:19]=[CH:20][C:14]=2[CH:13]=1)=[O:11])[CH3:7])[CH:2]([CH3:4])[CH3:3]>C(Cl)Cl.O=[Mn]=O>[CH2:1]([O:5][CH:6]([O:8][NH:9][C:10]([C:12]1[S:16][C:15]2[CH:17]=[C:18]([CH:21]=[O:22])[CH:19]=[CH:20][C:14]=2[CH:13]=1)=[O:11])[CH3:7])[CH:2]([CH3:4])[CH3:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 6-hydroxymethyl-benzo[b]thiophene-2-carboxylic acid (1-isobutoxy-ethoxy) amide (600 mg, 1.86 mmol) in DCM (3 mL) was added MnO2 (2.1 g, 24.1 mmol). The mixture was stirred at ambient temperature for 30 min and then filtered through celite. The filtrate was concentrated to afford the title compound (435 mg, 82%). LCMS m/z 320 [M+−H]+, 1H NMR (300 MHz, MeOD), δ: 0.94 (6H, d J=6.7 Hz, 2×CH3), 1.45 (3H, d J=5.3 Hz, CH3), 1.87 (1H, m, CH), 3.40 (2H, m, CH2), 5.08 (1H, dd J=5.2, 10.6 Hz, CH), 7.89-8.09 (3H, m, ArH), 8.55 (1H, s, ArH), 10.11 (1H, s, CHO).