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

HRID 2249008Notes

Reaction equation

Cl[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].C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C>>[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

Reactant 3

HCID 5948Tributylstannane

HCID 6547Azobisisobutyronitrile

HCID 54517612HCID 54517612, compound

Product 1

HCID 6993305S(-)-1-(PENTAFLUOROPHENYL)ETHANOLYield 66.2%

Conditions

Temperature: 80 °C

Procedure

A mixture of 1.23 g of (R)-(-)-2-chloro-1-(pentafluorophenyl)ethanol obtained in Example 8, 1.60 ml of tributyltin hydride, and 16 mg of AIBN was stirred for eight hours at 80° C. After completion of reaction, the reaction mixture was purified by silica gel column chromatography to give 0.7 g of (S)-(-)-1-(pentafluorophenyl)-ethanol.

Workup

customAfter completion of reaction
customthe reaction mixture was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-f6c1ed12612047a2aac580c204f1042d
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05041641

Reaction notes

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