Tributylstannane → S(-)-1-(PENTAFLUOROPHENYL)ETHANOL

HRID 2249007Notes

Reaction equation

HRID 2249007 reaction equation
Br[CH2:2][C@@H:3]([C:5]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]([F:14])[C:6]=1[F:15])[OH:4].BrC(C1C(F)=C(F)C(F)=C(F)C=1F)CO.C([SnH](CCCC)CCCC)CCC>CCCCCC>[F:11][C:10]1[C:5]([C@@H:3]([OH:4])[CH3:2])=[C:6]([F:15])[C:7]([F:14])=[C:8]([F:13])[C:9]=1[F:12]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 14645957HCID 14645957, compoundHCID 19995411HCID 19995411, compound

Product 1

HCID 6993305S(-)-1-(PENTAFLUOROPHENYL)ETHANOLYield 48.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 11.26 g of (R)-(-)-2-bromo-1-(pentafluorophenyl)ethanol containing 20% of 2-bromo-2-(pentafluorophenyl)ethanol obtained in Example 7 in 50 ml of hexane, was added 11.4 ml of tributyltin hydride at room temperature. After stirring for eight hours at 60° C., the reaction mixture was concentrated under reduced pressure, purified by silica gel column chromatography and distilled under reduced pressure to give 4.0 g of (S)-(-)-1-(pentafluorophenyl)ethanol having the following physical properties.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified by silica gel column chromatography
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-6cdc958240884f4d8223337fd7b62c25
Source dataset
uspto-grants-1991_08
Patent number
US05041641

Reaction notes

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