Dichloromethane methanol → 8-Fluoroisochroman-4-one
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][O:9][CH2:8][C:7]2=C.C[OH:14].C(Cl)Cl>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][O:9][CH2:8][C:7]2=[O:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
8-Fluoro-4-methylene-3,4-dihydro-1H-isochromene (400 mg) was dissolved in a solution of 1:1 MeOH/DCM (50 mL) and 1 mL of pyridine added. The mixture was chilled to −78° C. and ozone was bubbled through the mixture for 40 min. The reaction monitored by TLC. The mixture was purged with nitrogen at −78° C. for 10 min and then treated with PPh3. After concentration, the resulting residue was purified by preparative TLC to offer 300 mg of the title compound.
Workup
- additionadded
- customozone was bubbled through the mixture for 40 min
- customThe mixture was purged with nitrogen at −78° C. for 10 min
- additiontreated with PPh3
- concentrationAfter concentration
- customthe resulting residue was purified by preparative TLC
Sources & evidence
- ORD record
- ord-8f1c398c359b428d9bdb514bb3ab2a8e
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07884109B2
Reaction notes
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