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

HRID 2248999Notes

Reaction equation

HRID 2248999 reaction equation
[CH3:1][Al](C)C.[F:5][C:6]1[C:14]([F:15])=[C:13]([F:16])[C:12]([F:17])=[C:11]([F:18])[C:7]=1[CH:8]1[O:10][CH2:9]1>CCCCCC>[F:5][C:6]1[C:7]([CH:8]([CH3:1])[CH2:9][OH:10])=[C:11]([F:18])[C:12]([F:17])=[C:13]([F:16])[C:14]=1[F:15]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

To a 10 ml of ice-cooled 1M solution of trimethylaluminum in hexane, was added dropwise a solution of 1.05 g of (+)-2,3,4,5,6-pentafluorostyrene oxide (over 95%ee) in 5 ml of hexane, to react for five hours at 0° C and for another one hour at room temperature. 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 15%ee.

Workup

  1. customto react for five hours at 0° C and for another one hour at room temperature

Sources & evidence

ORD record
ord-86f20909e26642dbbaf15f2186ef2f76
Source dataset
uspto-grants-1991_08
Patent number
US05041641

Reaction notes

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