Water → {5-Methyl-4-[3-(trifluoromethyl)phenyl]furan-2-yl}methanol

HRID 1257438

Reaction equation

HRID 1257438 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7](OC)=[O:8])=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([CH2:7][OH:8])=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66939668Methyl 5-methyl-4-[3-(trifluoromethyl)phenyl]furan-2-carboxylate

Product 1

HCID 66939730{5-Methyl-4-[3-(trifluoromethyl)phenyl]furan-2-yl}methanolYield 88.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution (4 mL) of the compound (0.80 g) obtained in Example 128c in tetrahydrofuran was cooled in an ice bath, and lithium aluminum hydride (0.16 g) was added by small portions. The reaction mixture was stirred at the same temperature for 1 hr, water (0.16 mL), 15% sodium hydroxide (0.16 ml) and water (0.48 mL) were successively added, and the mixture was stirred at room temperature for 15 min. The insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (0.64 g) as a solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 min
  2. filtrationThe insoluble material was filtered off through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-81eb706833f34a9eb910c1929c7319dd
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Linked notes

Loading…