Sodium Hydroxide → 3,4-dihydro-4-oxo-8-propyl-7[2-[(5,6,7,8-tetrahydro-1-naphthalenyl)oxy]ethoxy]-2H-1-benzopyran-2,2-dipropanoic acid

HRID 2371641Notes

Reaction equation

HRID 2371641 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([O:15][CH2:16][CH2:17][O:18][C:19]3[C:28]4[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=4[CH:22]=[CH:21][CH:20]=3)=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][C:4]([CH2:36][CH2:37][C:38]([O:40]CC)=[O:39])([CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[CH2:3]1.[OH-].[Na+]>CO>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([O:15][CH2:16][CH2:17][O:18][C:19]3[C:28]4[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=4[CH:22]=[CH:21][CH:20]=3)=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][C:4]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])([CH2:36][CH2:37][C:38]([OH:40])=[O:39])[CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19907261diethyl 3,4-dihydro-4-oxo-8-propyl-7-[2-[(5,6,7,8-tetrahydro-1-naphthalenyl)oxy]ethoxy]-2H-1-benzopyran-2,2-dipropanoate

Product 1

HCID 199072623,4-dihydro-4-oxo-8-propyl-7[2-[(5,6,7,8-tetrahydro-1-naphthalenyl)oxy]ethoxy]-2H-1-benzopyran-2,2-dipropanoic acidYield 16.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 150 mg (0.277 mmol) of the titled product of Example 60, 3 ml of methanol, and 3 ml of 1N sodium hydroxide was stirred at reflux for one hour. The reaction mixture was permitted to cool and then partitioned between ethyl acetate and 3N hydrochloric acid. The aqueous layer was further extracted with two portions of ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered, and the solvent removed under reduced pressure. Crystallization of the residue from ethyl acetate gave 24 mg of the title compound as a solid, m.p. 159.5°-161.5° C.

Workup

  1. temperatureat reflux for one hour
  2. temperatureto cool
  3. custompartitioned between ethyl acetate and 3N hydrochloric acid
  4. extractionThe aqueous layer was further extracted with two portions of ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customCrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-9b1fce4bffea44be8ff54370dda6390c
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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