5-Formylfuran-2-boronic acid → {cis-5-[4-(Pentafluoro-lambda6-sulfanyl)phenyl]tetrahydrofuran-2-yl}methanol

HRID 718023Notes

Reaction equation

HRID 718023 reaction equation
[CH:1]([C:3]1[O:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].Br[C:12]1[CH:17]=[CH:16][C:15]([S:18]([F:23])([F:22])([F:21])([F:20])[F:19])=[CH:14][CH:13]=1>O.[Ru](=O)=O>[F:19][S:18]([F:20])([F:21])([F:22])([F:23])[C:15]1[CH:14]=[CH:13][C:12]([C@H:6]2[O:7][C@@H:3]([CH2:1][OH:2])[CH2:4][CH2:5]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 27343555-Formylfuran-2-boronic acidHCID 27791941-Bromo-4-(pentafluoro-lambda6-sulfanyl)benzene

Product 1

HCID 86713723{cis-5-[4-(Pentafluoro-lambda6-sulfanyl)phenyl]tetrahydrofuran-2-yl}methanol

Reagents, catalysts & solvents 1

HCID 16211523Ruthenium dioxide hydrateCatalyst

Procedure

The requisite {cis-5-[4-(pentafluoro-λ6-sulfanyl)phenyl]tetrahydrofuran-2-yl}methanol was prepared via Suzuki reaction of (5-formylfuran-2-yl)boronic acid with 1-bromo-4-(pentafluoro-λ6-sulfanyl)benzene, followed by hydrogenation in the presence of ruthenium(IV) oxide hydrate.

Sources & evidence

ORD record
ord-2efb9af4a4a84bc493dd27506deeda33
Source dataset
uspto-grants-2015_11
Patent number
US09193726B2

Reaction notes

Loading…