Water → 5-(3-(2-(7-Chloroquinolin-2-YL)ethenyl)phenyl)-4,6-dithianonanedioic acid

HRID 232411Notes

Reaction equation

HRID 232411 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:20]([S:28][CH2:29][CH2:30][C:31]([O:33]C)=[O:32])[S:21][CH2:22][CH2:23][C:24]([O:26]C)=[O:25])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Li+].O>COCCOC>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:20]([S:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[S:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 53731421Dimethyl 5-(3-(2-(7-chloroquinolin-2-yl)ethenyl)phenyl)-4,6-dithianonanedioate

Product 1

HCID 545297905-(3-(2-(7-Chloroquinolin-2-YL)ethenyl)phenyl)-4,6-dithianonanedioic acid

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of dimethyl ester (Step 2) (1.7 g) in 1,2-dimethoxyethane (60 ml) was added lithium hydroxide (10 ml of 2N). The reaction mixture was stirred overnight at room temperature. H2O (100 ml) was added and the 1,2-dimethoxyethane was removed under vacuo. The solution was extracted with ethylacetate (300 ml). The aqueous phase was acidified to pH 3, extracted with ethylacetate (200 ml), dried and evaporated. Flash chromatography of the residue using 5% EtOH in CH2Cl2 with 1% of acetic acid afforded the title compound.

Workup

  1. customthe 1,2-dimethoxyethane was removed under vacuo
  2. extractionThe solution was extracted with ethylacetate (300 ml)
  3. extractionextracted with ethylacetate (200 ml)
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-6e743f14817d49a38e9a4278e02ca318
Source dataset
uspto-grants-1989_07
Patent number
US04851409

Reaction notes

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