Lithium Hydroxide → HCID 22988679, compound

HRID 987262Notes

Reaction equation

HRID 987262 reaction equation
C([O:3][C:4](=[O:32])[CH:5]([O:29][CH2:30][CH3:31])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:9][CH:8]=1)C.[OH-].[Li+]>O1CCCC1.O.O>[CH2:30]([O:29][CH:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:11][CH:12]=1)[C:4]([OH:32])=[O:3])[CH3:31]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86595064HCID 86595064, compound

Product 1

HCID 22988679HCID 22988679, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

2-Ethoxy-3-{4-(4-(2-methanesulfonyloxyphenyl)butoxy]phenyl}propanoic acid ethyl ester (2.7 g; 5.8 mmole) was dissolved in tetrahydrofuran: water (1:3, 100 ml). Lithium hydroxide (0.36 g; 8.7 mmole) dissolved in a small amount of water was added. The reaction mixture was stirred over night at room temperature and then evaporated. The residue was redissolved in ethyl acetate and hydrochloric acid (2M) and extracted. After separation the organic phase was extracted with sodium hydroxide (1M, 30 ml). The water phase was cooled, acidified with hydrochloric acid (conc) and extracted with ethyl acetate. The organic phase was dried with magnesium sulfate and evaporation gave 2 g (79% yield) of 2-ethoxy-3-[4-(4-{2-methanesulfonyloxyphenyl}butoxy)phenyl]propanoic acid.

Workup

  1. additionwas added
  2. customevaporated
  3. dissolutionThe residue was redissolved in ethyl acetate
  4. extractionhydrochloric acid (2M) and extracted
  5. customAfter separation the organic phase
  6. extractionwas extracted with sodium hydroxide (1M, 30 ml)
  7. temperatureThe water phase was cooled
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic phase was dried with magnesium sulfate and evaporation

Sources & evidence

ORD record
ord-53fd6425b8e64c189268485db1a0c0f6
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

Loading…