Sodium Hydroxide → HCID 19004266, compound

HRID 2225807Notes

Reaction equation

HRID 2225807 reaction equation
C([O:3][C:4](=[O:29])[C:5](=[O:28])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14](=[O:27])[N:15]2[CH2:20][CH2:19][CH:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[CH:8][CH:7]=1)C.[OH-].[Na+]>CO>[O:27]=[C:14]([N:15]1[CH2:16][CH2:17][CH:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH2:20]1)[CH2:13][O:12][C:9]1[CH:8]=[CH:7][C:6]([C:5](=[O:28])[C:4]([OH:29])=[O:3])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54356254HCID 54356254, compound

Product 1

HCID 19004266HCID 19004266, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-[2-Oxo-2-(4-phenyl-1-piperidinyl)ethoxy]-alpha-oxobenzeneacetic acid ethyl ester (0.9 g) in methanol (80 mL) was treated with 1N sodium hydroxide solution (2.6 mL), and the mixture was stirred at room temperature for 25 minutes. After the methanol was evaporated under reduced pressure, water (25 mL) was added and the solution was acidified with 3N hydrochloric acid, then the aqueous layer was extracted with a dichloromethane-tetrahydrofuran mixture (35 mL; 5:2). The organic layer was dried (MgSO4), evaporated and the resulting solid was crystallized from dichloromethane-tetrahydrofuran-hexane and then from dichloromethane-tetrahydrofuran to furnish 0.25 g of 4-[2-oxo-2-(4-phenyl-1-piperidinyl)ethoxy]-alpha-oxobenzeneacetic acid, mp 209°-210° C. An additional 0.16 g of the acid was recovered from the mother liquor.

Workup

  1. customAfter the methanol was evaporated under reduced pressure, water (25 mL)
  2. additionwas added
  3. extractionthe aqueous layer was extracted with a dichloromethane-tetrahydrofuran mixture (35 mL; 5:2)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customthe resulting solid was crystallized from dichloromethane-tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-0733a7090c7f4bde91fe00c63347e66e
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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