Water → HCID 19699506, compound

HRID 863061Notes

Reaction equation

HRID 863061 reaction equation
[F:1][C:2]1[C:7]2[CH2:8][CH2:9][C:10](=[O:13])[CH2:11][CH2:12][C:6]=2[CH:5]=[C:4]([F:14])[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[C:7]2[CH2:8][CH2:9][CH:10]([OH:13])[CH2:11][CH2:12][C:6]=2[CH:5]=[C:4]([F:14])[CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19699282HCID 19699282, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19699506HCID 19699506, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

1,3-Difluoro-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-one (1.5 g, 7.6 mmol) was dissolved in 30 mL of dry THF, the solution was cooled to 0° C. under argon and 1M LAH (7.5 mL, 7.5 mmol) in THF was added over 2 minutes. The mixture was stirred at 0° C. for 1 hour and then 0.28 mL of water, 0.28 mL of 15% aqueous sodium hydroxide and 0.9 mL of water were added sequentially. The mixture was stirred for 5 minutes, filtered, washed with ethyl acetate and dried over magnesium sulfate. Evaporation of the solvents gave 1,3-difluoro-6,7,8,9-tetrahydro-7-hydroxy-5H-benzocycloheptene (1.55 g, 7.8 mmol) as an oil.

Workup

  1. stirringThe mixture was stirred for 5 minutes
  2. filtrationfiltered
  3. washwashed with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvents

Sources & evidence

ORD record
ord-5b9d60c946384d65bbd5464c83c7b4f3
Source dataset
uspto-grants-1998_02
Patent number
US05719280

Reaction notes

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