Lithium Hydroxide → HCID 25123286, compound

HRID 1361081Notes

Reaction equation

HRID 1361081 reaction equation
[OH-].[Li+].[CH2:3]([O:7][C:8]1[CH:9]=[C:10]([CH2:31][CH2:32][C:33]([O:35]C)=[O:34])[CH:11]=[CH:12][C:13]=1[CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])=[C:19]([O:29][CH3:30])[CH:18]=1)[CH2:4][CH2:5][CH3:6]>O1CCCC1>[CH2:3]([O:7][C:8]1[CH:9]=[C:10]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])[CH:11]=[CH:12][C:13]=1[CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][S:24]([CH2:27][CH3:28])(=[O:25])=[O:26])=[C:19]([O:29][CH3:30])[CH:18]=1)[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86642709HCID 86642709, compound

Product 1

HCID 25123286HCID 25123286, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

ml (0.85 mmol) of aqueous 1N lithium hydroxide solution are added to a solution of 259 mg (0.6 mmol) of methyl 3-{3-butoxy-4-[3-(4-ethanesulfonyloxy-3-methoxyphenyl)propyl]phenyl}propanoate in 3 ml of tetrahydrofuran. The reaction mixture is stirred at room temperature for 12 hours, concentrated and then taken up in water, acidified by adding hydrochloric acid solution and then extracted with ethyl acetate ethyl. The organic phases are combined, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and evaporated. After triturating in heptane, 208 mg (83%) of 3-{3-butoxy-4-[3-(4-ethanesulfonyloxy-3-methoxyphenyl)propyl]phenyl)propanoic acid are obtained in the form of white crystals with a melting point of 64° C.

Workup

  1. concentrationconcentrated
  2. additionby adding hydrochloric acid solution
  3. extractionextracted with ethyl acetate ethyl
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customAfter triturating in heptane

Sources & evidence

ORD record
ord-89f13a37082d468da31a6960b6f72f67
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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