Reaction #216354

ord-258ba8235ed3499a823646e01ed183ad

Reaction equation

C[C@H](O)[C@@]1(c2ccc(F)cc2F)CO1
(1S)-1-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol
O=c1[nH]nnn1-c1ccc(OCC(F)(F)C(F)(F)F)cc1
1-[4-(2,2,3,3,3-pentafluoropropoxy)phenyl]-5(1H,4H)-tetrazolone
→
C[C@@H](n1nnn(-c2ccc(OCC(F)(F)C(F)(F)F)cc2)c1=O)[C@@]1(c2ccc(F)cc2F)CO1
1-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-[4-(2,2,3,3,3-pentafluoropropoxy)phenyl]-5(1H,4H)-tetrazolone
Yield 69.4%

Reactants

C[C@H](O)[C@@]1(c2ccc(F)cc2F)CO1
(1S)-1-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol
O=c1[nH]nnn1-c1ccc(OCC(F)(F)C(F)(F)F)cc1
1-[4-(2,2,3,3,3-pentafluoropropoxy)phenyl]-5(1H,4H)-tetrazolone

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

In the same manner as in Reference Example 5, starting from 0.962 g of (1S)-1-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 1.19 g of 1-[4-(2,2,3,3,3-pentafluoropropoxy)phenyl]-5(1H,4H)-tetrazolone, 1.31 g of 1-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-[4-(2,2,3,3,3-pentafluoropropoxy)phenyl]-5(1H,4H)-tetrazolone was obtained as a colorless oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05466820uspto-grants-1995_11