HCID 58929618, compound → HCID 58929678, compound
Reaction equation
[F:1][C:2]1([F:10])[CH2:7][C@H:6]2[CH2:8][C@@H:3]1[CH2:4][C@@H:5]2[OH:9].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1([F:10])[CH2:7][C@H:6]2[CH2:8][C@@H:3]1[CH2:4][C:5]2=[O:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Silica gel 60 (particle size, 0.040-0.063 mm, CAS # 63231-67-4, from EMD Chemical Inc. 4.0 g) was added to a solution of (1R,2S,4R)-5,5-difluorobicyclo[2.2.1]heptan-2-ol (0.800 g, 5.40 mmol) in anhydrous dichloromethane (20.0 ml). The mixture was cooled to 0° C., and pyridinium chlorochromate (1.86 g, 8.64 mmol) was added. The reaction mixture was warmed to ambient temperature and stirred at this temperature overnight. After this time, the mixture was diluted with dichloromethane (30 mL) and then filtered through a pad of silica gel. Removal of the solvents gave the title compound as a white solid.
Workup
- temperatureThe reaction mixture was warmed to ambient temperature
- filtrationfiltered through a pad of silica gel
- customRemoval of the solvents
Sources & evidence
- ORD record
- ord-afb818d38a784ce8a4f13e133390a628
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541592B2
Reaction notes
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