Pyridinium chloride → 2-Butyl-6-fluoro-5-hydroxy-1-indanone

HRID 7888

Reaction equation

HRID 7888 reaction equation
[CH2:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([F:16])=[C:10]([O:14]C)[CH:11]=2)[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].Cl.N1C=CC=CC=1>>[CH2:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([F:16])=[C:10]([OH:14])[CH:11]=2)[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 119529412-Butyl-6-fluoro-5-methoxy-1-indanone

Product 1

HCID 219908852-Butyl-6-fluoro-5-hydroxy-1-indanoneYield 95.1%

Conditions

Temperature
200 °C

Procedure

A mixture of 2-butyl-6-fluoro-5-methoxy-1-indanone (2.0 g) and pyridine hydrochloride (15.0 g) was heated in an oil bath at 200° C. for 75 minutes. After cooling to room temperature, the mixture was partitioned between EtOAc (100 mL) and water (75 mL) containing brine (25 mL). The organic phase was washed with brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to provide 2-butyl-6-fluoro-5-hydroxy-1-indanone (1.79 g) as a solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between EtOAc (100 mL) and water (75 mL)
  3. additioncontaining brine (25 mL)
  4. washThe organic phase was washed with brine (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-1a97121dbeb748ada83910f7c64b7fb6
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Linked notes

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