2-(2,3,4,5,6-Pentafluorophenyl)oxirane → (+)-2-(Pentafluorophenyl)-1-propanol

HRID 2249000Notes

Reaction equation

HRID 2249000 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[CH:4]1[O:6][CH2:5]1.[CH3:15][Al](C)C>ClCCl.CCCCCC>[F:1][C:2]1[C:3]([CH:4]([CH3:15])[CH2:5][OH:6])=[C:7]([F:14])[C:8]([F:13])=[C:9]([F:12])[C:10]=1[F:11]

Participants

5

Reactant 2

HCID 27759812-(2,3,4,5,6-Pentafluorophenyl)oxiraneHCID 16682925Trimethylaluminum

Product 1

HCID 14651851(+)-2-(Pentafluorophenyl)-1-propanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 1.05 g of (+)-2,3,4,5,6-pentafluorostyrene oxide (over 95%ee) in 10 ml of dichloromethane, was added a 6 ml of 1.0M solution of trimethylalumimum in hexane, to react for one hour at 40° C. The similar work-up to Example 1 gave 1.10 g of (+)-2-(pentafluorophenyl)-1-propanol. The specific rotation was compared with that of Example 1, and the optical purity was determined to be 69%ee.

Workup

  1. customto react for one hour at 40° C

Sources & evidence

ORD record
ord-478467707c734e5dbab565379adffd29
Source dataset
uspto-grants-1991_08
Patent number
US05041641

Reaction notes

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