Ammonium Chloride → 5-(5-Fluoro-2-methoxyphenyl)-5-methyl-3-(trifluoromethyl)hexane-2,3-diol

HRID 2055026Notes

Reaction equation

HRID 2055026 reaction equation
C[Mg]Cl.O1CCC[CH2:5]1.[F:9][C:10]1[CH:11]=[CH:12][C:13]([O:28][CH3:29])=[C:14]([C:16]([CH3:27])([CH3:26])[CH2:17][C:18]([OH:25])([C:21]([F:24])([F:23])[F:22])[CH:19]=[O:20])[CH:15]=1.[Cl-].[NH4+]>C(OCC)C>[F:9][C:10]1[CH:11]=[CH:12][C:13]([O:28][CH3:29])=[C:14]([C:16]([CH3:27])([CH3:26])[CH2:17][C:18]([C:21]([F:24])([F:23])[F:22])([OH:25])[CH:19]([OH:20])[CH3:5])[CH:15]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 115731224-(5-Fluoro-2-methoxy-phenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalHCID 178420676HCID 178420676, compound

Product 1

HCID 219488565-(5-Fluoro-2-methoxyphenyl)-5-methyl-3-(trifluoromethyl)hexane-2,3-diol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

8 ml of 3 M methylmagnesium chloride-tetrahydrofuran solution is added in drops to the solution of 3.6 mg (11.7 mmol) of 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal in 150 ml of diethyl ether at +2° C. Stirring is continued for 1 hour at +2° C. and for 2 hours at room temperature. Then, it is hydrolyzed with saturated ammonium chloride solution while being cooled with ice, the organic phase is separated, dried on sodium sulfate and concentrated by evaporation. Column chromatography on silica gel with hexane-ethyl acetate yields 2.23 g of the product.

Workup

  1. temperaturewhile being cooled with ice
  2. customthe organic phase is separated
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-a64393afe31f44ada0017951efc9656a
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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