Water → 7-Oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylic Acid
Reaction equation
[S:1]1[C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]2[CH2:9][CH2:10][CH2:11][CH2:12][C:2]1=2.O.[N+]([O-])([O-])=[O:15].[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>C(O)(=O)C>[O:15]=[C:12]1[C:2]2[S:1][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[CH2:9][CH2:10][CH2:11]1Participants
Procedure
A 25-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylic acid (3.00 g, 16.5 mmol), acetic acid (40 mL) and water (40 mL). A solution of ammonium cerium(IV) nitrate (36.1 g, 65.9 mmol) in acetic acid (40 mL) was added dropwise, and the reaction was stirred at room temperature for 1 h. After this time, the reaction mixture was poured into water (200 mL) and extracted with methylene chloride (3×200 mL). The organic extracts were combined, dried over sodium sulfate, filtered and the solvent removed under reduced pressure to afford 16 in 72% yield (2.35 g) as a yellow solid: mp 174-175° C.; 1H NMR (500 MHz, DMSO-d6) δ 13.60 (bs, 1H), 7.68 (s, 1H), 2.86 (t, 2H, J=6.0 Hz), 2.59 (t, 2H, J=6.0 Hz), 2.08 (quintet, 2H, J=6.0 Hz).
Workup
- customA 25-mL single-neck round-bottomed flask equipped with a magnetic stirrer
- customwas purged with nitrogen
- extractionextracted with methylene chloride (3×200 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customthe solvent removed under reduced pressure
Sources & evidence
- ORD record
- ord-a877e0300dd24b20ad3cf739a84991c5
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07884108B2
Reaction notes
Loading…