Sodium Hydroxide → HCID 18695841, compound

HRID 1415670Notes

Reaction equation

HRID 1415670 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 mM) of lithium aluminum hydride were added in portions to 9.4 g (38 mM) of 4-p-fluorophenyl-1-cyclohexene-1,2-dicarboximide in 300 ml of tetrahydrofuran at room temperature while stirring vigorously over the course of 45 min. The mixture was stirred for 0.5 h and refluxed for 6 h. After cooling, ten percent sodium hydroxide solution was cautiously added dropwise while cooling in ice and stirring vigorously, and the precipitated hydroxides were filtered off with suction and washed with tetrahydrofuran. The filtrate was evaporated 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, after which the acidic aqueous phase was made alkaline again 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. stirringThe mixture was stirred for 0.5 h
  2. temperaturerefluxed for 6 h
  3. temperatureAfter cooling
  4. temperaturewhile cooling in ice
  5. stirringstirring vigorously
  6. filtrationthe precipitated hydroxides were filtered off with suction
  7. washwashed with tetrahydrofuran
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was partitioned between water and methyl t-butyl ether at pH=10
  10. extractionThe organic phase was subsequently extracted twice with ten percent hydrochloric acid
  11. extractionIt was then extracted twice with methyl t-butyl ether
  12. customAfter drying
  13. concentrationconcentration

Sources & evidence

ORD record
ord-affff63ecc6943e3a39bb6ff764f104f
Source dataset
uspto-grants-1999_06
Patent number
US05908844

Reaction notes

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