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 916001Notes

Reaction equation

HRID 916001 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 at reflux for 3 hours 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 water was removed by drying 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. temperatureat reflux for 3 hours
  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. customThe water was removed
  9. dry with materialby drying over magnesium sulfate and 300 mL of EtOAc
  10. additionwas added
  11. waitAfter 1 hour
  12. filtrationthe mixture was filtered through diatomaceous earth
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6cfca9cb3d17467fad3631603509bc79
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

Loading…