Sodium Bicarbonate → HCID 131727830, compound

HRID 1443186Notes

Reaction equation

HRID 1443186 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-9bf117e8298647469fb928641bd78c90
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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