Sodium Bicarbonate → HCID 131727830, compound

HRID 1869370Notes

Reaction equation

HRID 1869370 reaction equation
C([O:3][C:4](=O)[C:5]([OH:22])([C:18]([F:21])([F:20])[F:19])[CH2:6][C:7](C1C=C(F)C=CC=1F)([CH3:9])[CH3:8])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O-])(O)=O.[Na+]>C(OCC)C.C(OCC)(=O)C>[CH3:8][CH:7]([CH3:9])[CH2:6][C:5]([C:18]([F:19])([F:20])[F:21])([OH:22])[CH2:4][OH:3]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 17989210HCID 17989210, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 131727830HCID 131727830, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.4 g (15.5 mmol) of 4-(2,5-difluorophenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-valeric acid ethyl ester (WO 02/10143) is dissolved at 0° C. in diethyl ether and mixed within 20 minutes with 1.76 g (46.5 mmol) of lithium aluminum hydride. It is allowed to stir at room temperature for 4 hours, and then enough saturated NaHCO3 solution is carefully added until no more gas generation can be observed. The mixture is diluted with ethyl acetate, stirred for 15 more minutes, and then the formed precipitate is filtered off. It is concentrated by evaporation and chromatographed on silica gel with hexane/ethyl acetate (50%). 2.45 g of 2,5-difluorophenyl)-4-methyl-2-trifluoromethyl-pentane-1,2-diol is obtained as a weakly yellowish crystallizing oil.

Workup

  1. stirringstirred for 15 more minutes
  2. filtrationthe formed precipitate is filtered off
  3. concentrationIt is concentrated by evaporation
  4. customchromatographed on silica gel with hexane/ethyl acetate (50%)

Sources & evidence

ORD record
ord-ee4b76e495a6488f8e2be301f3c7fa06
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

Loading…