Lithium Hydroxide → HCID 11568655, compound

HRID 852353Notes

Reaction equation

HRID 852353 reaction equation
C([O:3][C:4](=[O:33])[C:5]([CH3:32])([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH2:15][CH2:16][CH2:17][C:18]#[C:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=2)=[CH:10][C:9]=1[CH3:31])[CH3:6])C.[Li+].[OH-]>C1COCC1.CCO.CCOCC>[CH3:32][C:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH2:15][CH2:16][CH2:17][C:18]#[C:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:24][CH:25]=2)=[CH:10][C:9]=1[CH3:31])([CH3:6])[C:4]([OH:33])=[O:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69460245HCID 69460245, compound

Product 1

HCID 11568655HCID 11568655, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.105 g (0.22 mmol) of the above prepared 2-methyl-2-{2-methyl-4-[5-(4-trifluoromethoxy-phenyl)-pent-4-ynylsulfanyl]-phenoxy}-propionic acid ethyl ester was dissolved in 4 ml of THF/EtOH (1:1), treated at 0° C. with 0.66 ml (0.66 mmol) of 1N LiOH, and kept at ambient temperature for 22 h. The reaction mixture was taken up in ether and washed with aqueous 10% KHSO4 solution and aqueous 10% NaCl solution. The water phases were extracted with ether (two times). The organic phase was dried (Na2SO4) and evaporated. The crude product was precipitated in pentane (RT to 4° C.) and decanted to give 28 mg of the title compound as colorless oil.

Workup

  1. washwashed with aqueous 10% KHSO4 solution and aqueous 10% NaCl solution
  2. extractionThe water phases were extracted with ether (two times)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated
  5. customThe crude product was precipitated in pentane (RT to 4° C.)
  6. customdecanted

Sources & evidence

ORD record
ord-79628b1bf9fc41478073a32d004edfdd
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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