Lithium hydroxide, monohydrate → 2-Ethoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)-2-nitropheny]propanoic acid

HRID 987268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 987268
C[O:2][C:3](=[O:32])[CH:4]([O:29][CH2:30][CH3:31])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=2)=[CH:8][C:7]=1[N+:26]([O-:28])=[O:27].O.[OH-].[Li+]>O1CCCC1.O>[CH2:30]([O:29][CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=2)=[CH:8][C:7]=1[N+:26]([O-:28])=[O:27])[C:3]([OH:32])=[O:2])[CH3:31]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 571861342-Ethoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)-2-nitrophenyl]propanoic acid methyl ester

Produkt 1

HCID 229886802-Ethoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)-2-nitropheny]propanoic acidAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Ethoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)-2-nitrophenyl]propanoic acid methyl ester (described in Example 35) (0.8 g; 1.71 mmole) was dissolved in tetrahydrofuran (8 ml). A solution of lithium hydroxide monohydrate (0.086 g; 2.05 mmole) in water (8 ml) was added under stirring. The reaction mixture was stirred at room temperature for 5 hours and then evaporated to remove tetrahydrofuran. The residue was extracted with diethyl ether, acidified to pH˜3 with hydrochloric acid (10%) and extracted with ethyl acetate. The organic phase was washed with water and brine, dried with magnesium sulfate. The solvent was removed and 0.72 g (93% yield) of 2-ethoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)-2-nitropheny]propanoic acid was obtained.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 5 hours
  2. customevaporated
  3. customto remove tetrahydrofuran
  4. extractionThe residue was extracted with diethyl ether
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried with magnesium sulfate
  8. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-294ea424d0564700b3db5de53f1bf708
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630600B1

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