Triphenylphosphine → 3-(1-((tert-butyldimethylsilyl)oxy)ethyl)-1-oxo-1H-isochromene-4-carbaldehyde
Reaction equation
[O:1]=[O+][O-].[Si:4]([O:11][CH:12]([C:14]1[O:15][C:16](=[O:26])[C:17]2[C:22]([C:23]=1[CH:24]=C)=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:13])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O=O.C(Cl)Cl>[Si:4]([O:11][CH:12]([C:14]1[O:15][C:16](=[O:26])[C:17]2[C:22]([C:23]=1[CH:24]=[O:1])=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:13])([C:7]([CH3:10])([CH3:8])[CH3:9])([CH3:6])[CH3:5]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A slow stream of O3 in O2 was passed through a −78° C. cooled solution of 3-(1-((tert-butyldimethylsilyl)oxy)ethyl)-4-vinyl-1H-isochromen-1-one (intermediate B59.1, 2.967 g of crude) in DCM (100 ml) for 1.5 hrs. The excess of 03 was purged by N2 bubbling, then a solution of PPh3 (2.316 g, 8.83 mmol) in DCM (20 ml) was added. The solution was allowed to reach 25° C. and it was stirred overnight. The solvent was removed in vacuo and the crude material was purified by flash chromatography on Biotage silica gel cartridge (cyclohexane to cyclohexane:EtOAc=90:10) to afford 3-(1-((tert-butyldimethylsilyl)oxy)ethyl)-1-oxo-1H-isochromene-4-carbaldehyde (Intermediate B59.2, 1.453 g, 4.38 mmol).
Workup
- customwas passed through a −78° C.
- customThe excess of 03 was purged by N2 bubbling
- customto reach 25° C.
- customThe solvent was removed in vacuo
- customthe crude material was purified by flash chromatography on Biotage silica gel cartridge (cyclohexane to cyclohexane:EtOAc=90:10)
Sources & evidence
- ORD record
- ord-9aff995c9d3145619bccc0ce172beb89
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321776B2
Reaction notes
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