4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester → 2-Hydroxy-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-pentanol

HRID 2080565Notes

Reaction equation

HRID 2080565 reaction equation
C([O:3][C:4](=O)[C:5]([OH:23])([C:19]([F:22])([F:21])[F:20])[CH2:6][C:7]([C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[O:17][CH3:18])([CH3:9])[CH3:8])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:16][C:14]1[CH:13]=[CH:12][C:11]([O:17][CH3:18])=[C:10]([C:7]([CH3:9])([CH3:8])[CH2:6][C:5]([C:19]([F:21])([F:22])[F:20])([OH:23])[CH2:4][OH:3])[CH:15]=1

Participants

4

Reactant 2

HCID 179356104-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 219489282-Hydroxy-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-pentanolYield 92.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a chilled solution (ice-water bath) of 6 g (17.0 mmol) of the above 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester in 60 mL of dry THF, 2.4 g (61.5 mmol) of lithium aluminum hydride was added in portions. After the addition, the cold bath was removed and the mixture was stirred at room temperature overnight. The mixture was then warmed to reflux for 3 hour and then cautiously quenched by slow addition to 100 mL of THF containing 2 mL of water. Additional water was then cautiously added for a total of 15 mL and the resulting mixture stirred for 2 hours. The excess water was dried over magnesium sulfate and 300 mL of EtOAc was added. After 1 hour, the mixture was filtered through diatomaceous earth and concentrated in vacuo to afford 4.9 g (92%) of 4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethylpentane-1,2-diol as an oil.

Workup

  1. additionAfter the addition
  2. customthe cold bath was removed
  3. temperatureThe mixture was then warmed
  4. temperatureto reflux for 3 hour
  5. customcautiously quenched by slow addition to 100 mL of THF containing 2 mL of water
  6. additionAdditional water was then cautiously added for a total of 15 mL
  7. stirringthe resulting mixture stirred for 2 hours
  8. dry with materialThe excess water was dried over magnesium sulfate and 300 mL of EtOAc
  9. additionwas added
  10. waitAfter 1 hour
  11. filtrationthe mixture was filtered through diatomaceous earth
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f97d347ae6fd4c9db6209096be2e88e2
Source dataset
uspto-grants-2011_04
Patent number
US07932392B2

Reaction notes

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