Ethyl Acetate → 5-Fluoro-1-benzothiophene-2-carbaldehyde
Reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]2[S:6][C:7]([CH2:9][OH:10])=[CH:8][C:4]=2[CH:3]=1.C(OCC)(=O)C>C(Cl)Cl.CCCCCC.O=[Mn]=O>[F:1][C:2]1[CH:12]=[CH:11][C:5]2[S:6][C:7]([CH:9]=[O:10])=[CH:8][C:4]=2[CH:3]=1Participants
6
Conditions
- Temperature
- 52 °C
Procedure
MnO2 (4.298 g, 49.45 mmol) was added to a solution of (5-fluorobenzo[b]-thiophen-2-yl)methanol (I-50b: 1.8 g, 9.89 mmol) in DCM (50 mL) and the resulting reaction mass was stirred at 52° C. for 2 hours. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mass was cooled to room temperature, filtered off the catalyst through a celite bed and washed the celite bed with DCM. The filtrate was concentrated under reduced pressure and dried under vacuum to afford 1.5 g of the product (88.23% yield).
Workup
- customthe resulting reaction mass
- temperatureThe reaction mass was cooled to room temperature
- filtrationfiltered off the catalyst through a celite bed
- washwashed the celite bed with DCM
- concentrationThe filtrate was concentrated under reduced pressure
- customdried under vacuum
Sources & evidence
- ORD record
- ord-44484fc5167b4cf7b4b49dad50a40413
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946260B2
Reaction notes
Loading…