Sodium Bicarbonate → HCID 17989217, compound

HRID 1443130Notes

Reaction equation

HRID 1443130 reaction equation
C([O:3][C:4](=O)[C:5]([C:24]([F:27])([F:26])[F:25])([O:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=1[O:17][CH3:18])([CH3:9])[CH3:8])C.[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O-])(O)=O.[Na+]>C(OCC)C>[F:16][C:12]1[C:11]([O:17][CH3:18])=[C:10]([C:7]([CH3:8])([CH3:9])[CH2:6][C:5]([C:24]([F:26])([F:27])[F:25])([O:19][Si:20]([CH3:22])([CH3:23])[CH3:21])[CH2:4][OH:3])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 17989124HCID 17989124, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 17989217HCID 17989217, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5.24 g (12.34 mmol) of 4-(3-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-2-trimethylsilyloxy-pentanoic acid ethyl ester is dissolved in 45 ml of diethyl ether and mixed at 0 to 5° C. in portions with 936.9 mg (24.69 mmol) of LiAlH4. After four and one-half hours of stirring at room temperature, the reaction mixture is carefully mixed with saturated NaHCO3 while being cooled in an ice bath, stirred for one hour under cold conditions and overnight at room temperature. After the usual working-up, 4.11 g (87.1%) of a mixture that consists of the desired compound and the compound in which the silyl ether has migrated is obtained. The mixture is incorporated in crude form into the next stage.

Workup

  1. temperaturewhile being cooled in an ice bath
  2. stirringstirred for one hour under cold conditions and overnight at room temperature

Sources & evidence

ORD record
ord-258f984cca194047bda9155b54c236a7
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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