Sodium Hydroxide → HCID 18695841, compound

HRID 1941234Notes

Reaction equation

HRID 1941234 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][C:17]3[C:20]([NH:22][C:23](=O)[C:16]=3[CH2:15]2)=O)=[CH:10][CH:9]=1.[OH-].[Na+]>O1CCCC1>[F:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]2[CH2:19][CH2:18][C:17]3[CH:15]2[CH2:16][CH2:23][NH:22][CH:20]=3)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86751776HCID 86751776, compound

Product 1

HCID 18695841HCID 18695841, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.5 g (118 mmol) of lithium aluminum hydride were added in portions to 9.4 g (38 mmol) of 4-p-fluorophenylcyclohex-1-ene-1,2-dicarboximide in 300 ml of tetrahydrofuran during the course of 45 min at room temperature and with good stirring. After stirring for 0.5 h, the mixture was refluxed for a further 6 h. After cooling, ten percent sodium hydroxide solution was carefully added dropwise with good stirring and with ice cooling and the precipitated hydroxides were filtered off with suction and washed with tetrahydrofuran. The filtrate was concentrated to dryness and the residue was partitioned between water and methyl t-butyl ether at pH=10. The organic phase was subsequently extracted twice with ten percent hydrochloric acid and the acidic aqueous phase was rendered alkaline again after this with concentrated sodium hydroxide solution. It was then extracted twice with methyl t-butyl ether. After drying and concentration, 1.8 g (22%) of product were isolated as a pale oil.

Workup

  1. temperaturethe mixture was refluxed for a further 6 h
  2. temperatureAfter cooling
  3. stirringwith good stirring and with ice cooling
  4. filtrationthe precipitated hydroxides were filtered off with suction
  5. washwashed with tetrahydrofuran
  6. concentrationThe filtrate was concentrated to dryness
  7. customthe residue was partitioned between water and methyl t-butyl ether at pH=10
  8. extractionThe organic phase was subsequently extracted twice with ten percent hydrochloric acid
  9. extractionIt was then extracted twice with methyl t-butyl ether
  10. customAfter drying
  11. concentrationconcentration

Sources & evidence

ORD record
ord-7e3760591c234a60a2717e1f3e227697
Source dataset
uspto-grants-1997_12
Patent number
US05703091

Reaction notes

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