Sodium Hydroxide → HCID 70242910, compound

HRID 1067139Notes

Reaction equation

HRID 1067139 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:19]([CH2:24][C:25]4[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=4[C:27]([O:29]C)=[O:28])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+:36]>CO.O1CCOCC1.Cl>[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:19]([CH2:24][C:25]4[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=4[C:27]([O-:29])=[O:28])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[Na+:36]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21196497HCID 21196497, compound

Product 1

HCID 70242910HCID 70242910, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21966525Dioxane MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 2-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoate (37 mg) in MeOH-1,4-dioxane (1:1, 3 ml) was added iN NaOH solution (1.0 ml) at 5° C. and the mixture was stirred at 80° C. for 3 hours. After cooling, the mixture was acidified with iN HCl and extracted with EtOAc. The organic layer was washed with water and brine, dried over magnesium sulfate, evaporated in vacuo. The residue was dissolved in MeOH-1,4-dioxane (1:1, 2 ml) and 1N NaOH solution (0.0824 ml) was added thereto. The mixture was evaporated and Et2 was added. The resulting solid was collected by filtration to give sodium 2-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl1methyl}benzoate (19.9 mg).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in MeOH-1,4-dioxane (1:1, 2 ml)
  7. addition1N NaOH solution (0.0824 ml) was added
  8. customThe mixture was evaporated
  9. additionEt2 was added
  10. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-948eb6582ada4778a0b691f37138c421
Source dataset
uspto-grants-2001_06
Patent number
US06245790B1

Reaction notes

Loading…