Sodium Bicarbonate → HCID 17989217, compound

HRID 1444397Notes

Reaction equation

HRID 1444397 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 stirred in an ice bath, stirred for one hour under cold conditions and overnight at room temperature. After the conventional working-up, 4.11 g (87.1%) of a mixture that consists of the desired compound and the compound is obtained, in which the silyl ether has migrated. The mixture is incorporated in crude form into the next stage.

Workup

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

Sources & evidence

ORD record
ord-c7b61e382b9e48b7b8a91e4f0c1c0720
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

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