Water → HCID 9935613, compound

HRID 1110915Notes

Reaction equation

HRID 1110915 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][CH2:6][C:7]1([CH3:38])[CH2:12][C:11](=[O:13])[C:10]2[CH:14]=[CH:15][C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][C:28]4[CH:37]=[CH:36][C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[N:29]=4)[CH:21]=3)=[CH:17][C:9]=2[O:8]1)C.O.[OH-].[Li+].O1CCCC1.O>CO>[N:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:36]=[CH:37][C:28]=1[CH2:27][O:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[CH2:19][O:18][C:16]1[CH:15]=[CH:14][C:10]2[C:11](=[O:13])[CH2:12][C:7]([CH2:6][CH2:5][C:4]([OH:39])=[O:3])([CH3:38])[O:8][C:9]=2[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 19913886HCID 19913886, compound

Product 1

HCID 9935613HCID 9935613, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.6 g of ethyl-3-(7-(3-(quinolin-2-ylmethoxy)benzyloxy)-3,4-dihydro-2-methyl-4-oxo-2H-1-benzopyran-2-yl)propanoate and 1.02 g of lithium hydroxide hydrate are combined in 30 ml of methanol, 30 ml of tetrahydrofuran and 10 ml of water and stirred at room temperature for 3 hours. The solvent is removed by evaporation and the residue diluted with water and washed with ether. The pH of the aqueous portion is adjusted to 5 and the suspension extracted with ethyl acetate. The dried ethyl acetate solution is concentrated and the residue purified by chromatography on silica gel to give 0.85 g of 3-(7-(3-(quinolin-2-ylmethoxy)benzyloxy)-3,4-dihydro-2-methyl-4-oxo-2H-1-benzopyran-2-yl)propanoic acid; m.p. 152°-54° C.

Workup

  1. customThe solvent is removed by evaporation
  2. additionthe residue diluted with water
  3. washwashed with ether
  4. extractionthe suspension extracted with ethyl acetate
  5. concentrationThe dried ethyl acetate solution is concentrated
  6. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-6b33b721686c412294cf61434c2405a7
Source dataset
uspto-grants-1990_12
Patent number
US04977162

Reaction notes

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