Lithium Hydroxide → 3-{7-[3-(4-Acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-methyl-4-oxo-8-propyl-3,4-dihydro-2H-1-benzopyran-2-yl}propanoic acid

HRID 868375Notes

Reaction equation

HRID 868375 reaction equation
[OH-].[Li+].[C:3]([C:6]1[CH:37]=[CH:36][C:9]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:32]=[CH:31][C:18]3[C:19](=[O:30])[CH2:20][C:21]([CH2:24][CH2:25][C:26]([O:28]C)=[O:27])([CH3:23])[O:22][C:17]=3[C:16]=2[CH2:33][CH2:34][CH3:35])=[C:8]([CH2:38][CH2:39][CH3:40])[C:7]=1[OH:41])(=[O:5])[CH3:4]>O.O1CCCC1.CO>[C:3]([C:6]1[CH:37]=[CH:36][C:9]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:32]=[CH:31][C:18]3[C:19](=[O:30])[CH2:20][C:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])([CH3:23])[O:22][C:17]=3[C:16]=2[CH2:33][CH2:34][CH3:35])=[C:8]([CH2:38][CH2:39][CH3:40])[C:7]=1[OH:41])(=[O:5])[CH3:4]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 13920733HCID 13920733, compound

Product 1

HCID 1271043-{7-[3-(4-Acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-methyl-4-oxo-8-propyl-3,4-dihydro-2H-1-benzopyran-2-yl}propanoic acidYield 89.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.5 g (9.5 mmole) of lithium hydroxide in 10 ml of water was added to a solution of 2.2 g (3.9 mmole) of the title compound of Example 6 in 25 ml of tetrahydrofuran and 20 ml of methanol. After the reaction mixture was stirred for 3 hours at room temperature, the solvent was evaporated and water was added to the residue. After extracting with a small amount of diethyl ether, the aqueous layer was acidified with dilute hydrochloric acid and allowed to stand in the cold overnight. The solid was filtered, washed with water and recrystallized from ethyl acetate/hexane to yield 1.83 g of the title compound, mp. 80°-83°. Structure assignment was confirmed by nmr and infrared spectra and by elemental analysis. nmr (CDCl3) loss of ester CH3 (compare Example 6)

Workup

  1. customthe solvent was evaporated
  2. additionwater was added to the residue
  3. extractionAfter extracting with a small amount of diethyl ether
  4. customto stand in the cold overnight
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e87b906815e3404f82e14e74ef068700
Source dataset
uspto-grants-1988_10
Patent number
US04778903

Reaction notes

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