Phosphate → HCID 54517612, compound
Reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]([F:14])[C:3]=1[C@H:4]1[O:6][CH2:5]1.[Cl-:15].[Li+].P([O-])([O-])([O-])=O>O1CCCC1>[Cl:15][CH2:5][C@@H:4]([C:3]1[C:2]([F:1])=[C:10]([F:11])[C:9]([F:12])=[C:8]([F:13])[C:7]=1[F:14])[OH:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To an ice-cooled solution of 10.51 g of (R)-(+)-2,3,4,5,6-pentafluorostyrene oxide was dissolved in 100 ml of tetrahydrofuran, was added dropwise a solution of Li2CuCl4, which was prepared by adding 10.08 g of cupric chloride to a suspension of 6.36 g of lithium chloride in 150 ml of tetrahydrofuran. After completion of addition, the solution was stirred for 20 hours at room temperature. The resulted reaction mixture was poured into a 0.05 mol phosphate buffer, and was extracted with ether. The resulted extract was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure, thereby obtaining 12.00 g of (R)-(-)-2-chloro-1-(pentafluorophenyl)ethanol containing 20% of (+)-2-chloro-2-(pentafluorophenyl)ethanol. This was subjected to isolation by silica gel column chromatography, thereby obtaining (R)-(-)-2-chloro-1-(pentafluorophenyl)-ethanol and (+)-2-chloro-2-(pentafluorophenyl)ethanol respectively possessing the aforementioned physical properties.
Workup
- customwas prepared
- additionAfter completion of addition
- customThe resulted reaction mixture
- extractionwas extracted with ether
- extractionThe resulted extract
- dry with materialwas dried over magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-21453e76d9b34afa83274384b7114d3e
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05041641
Reaction notes
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