Tetrahydrofuran → HCID 9863870, compound

HRID 322102Notes

Reaction equation

HRID 322102 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:20]=[C:19]3[C:15]([C:16]([CH2:28][CH3:29])=[N:17][N:18]3[C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[CH:14][CH:13]=2)=[CH:8][CH2:7]1)=[O:5])C.O1CCCC1.[OH-].[Na+]>CO>[CH2:28]([C:16]1[C:15]2[C:19](=[CH:20][C:12]([C:9]3[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH:8]=3)=[CH:13][CH:14]=2)[N:18]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)[N:17]=1)[CH3:29]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 9886817HCID 9886817, compound

Product 1

HCID 9863870HCID 9863870, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1.13 g (2.87 mmol) of 4-(3-ethyl-1-(4-fluorophenyl)-1H-indazol-6-yl)-cyclohex-3-ene-carboxylic acid ethyl ester dissolved in 50 mL of methanol and 15 mL of tetrahydrofuran was added 8.62 mL (8.61 mmol) of 1N sodium hydroxide and reaction mixture heated to reflux for 3 hr. After 3 hr, the reaction mixture was concentrated on a rotary evaporator, diluted with 200 mL of H2O, acidified to pH 1 with 1N HCl and extracted 2×200 mL ethyl acetate. The organic extracts were combined, washed with water, brine and dried over Na2SO4. Filtration, concentration and drying gave crude product. Recrystallization from ethyl acetate/hexane gave 0.31 grams of white crystalline product. mp=214-216° C.; MS, m/z 365 (M+H+, base).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hr
  3. concentrationthe reaction mixture was concentrated on a rotary evaporator
  4. additiondiluted with 200 mL of H2O
  5. extractionextracted 2×200 mL ethyl acetate
  6. washwashed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationFiltration, concentration
  9. customdrying
  10. customgave crude product
  11. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a2e3f3d5bdb9488cae804c720ceee403
Source dataset
uspto-grants-2001_04
Patent number
US06211222B1

Reaction notes

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