Tetrahydrofuran → HCID 9927951, compound

HRID 741769Notes

Reaction equation

HRID 741769 reaction equation
[C:1]([C:3]1([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:14]=2)[CH2:8][CH2:7][C:6]([C:9]([O:11]C)=[O:10])=[CH:5][CH2:4]1)#[N:2].O1CCCC1.[OH-].[K+]>CO.O>[C:1]([C:3]1([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:14]=2)[CH2:8][CH2:7][C:6]([C:9]([OH:11])=[O:10])=[CH:5][CH2:4]1)#[N:2]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 9863466HCID 9863466, compound

Product 1

HCID 9927951HCID 9927951, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of methyl 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohex-1-ene-1-carboxylate (0.07 g, 0.18 mmol) in methanol (0.5 mL, containing just enough tetrahydrofuran to solubilize the ester) under an argon atmosphere was added a solution of potassium hydroxide (0.03 g, 0.55 mmol) in water (0.4 mL). The resulting mixture was stirred at room temperature for 4h, then poured into water and extracted with ethyl acetate. The aqueous phase was acidified with 3N hydrochloric acid and extracted twice with ethyl acetate. The organic phase from the acid extraction was dried (sodium sulfate) and concentrated under reduced pressure to provide a viscous oil, which solidified upon standing. The solid was recrystallized from hexanes/methylene chloride (0.05 g, 82%): m.p. 161°-163 ° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted twice with ethyl acetate
  3. extractionThe organic phase from the acid extraction
  4. dry with materialwas dried (sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customto provide a viscous oil, which
  7. customThe solid was recrystallized from hexanes/methylene chloride (0.05 g, 82%)

Sources & evidence

ORD record
ord-ae57d65ee2b743c5b185fbdfefd24955
Source dataset
uspto-grants-1996_09
Patent number
US05552438

Reaction notes

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