Lithium Hydroxide → HCID 67581421, compound

HRID 1957706Notes

Reaction equation

HRID 1957706 reaction equation
[OH:1][CH:2]([C:15]1[CH:20]=[C:19]([C:21]23[CH2:30][CH:25]4[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]4)[CH2:22]2)[CH2:28]3)[C:18]([O:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37])=[CH:17][C:16]=1[O:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH3:44])[C:3]#[C:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][CH:6]=1.[OH-].[Li+]>C1COCC1>[OH:1][CH:2]([C:15]1[CH:20]=[C:19]([C:21]23[CH2:30][CH:25]4[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]4)[CH2:22]2)[CH2:28]3)[C:18]([O:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37])=[CH:17][C:16]=1[O:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH3:44])[C:3]#[C:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([OH:11])=[O:10])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67663021HCID 67663021, compound

Product 1

HCID 67581421HCID 67581421, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

800 mg (1.3 mmol) of the above methyl ester (e), 340 mg (7.8 mmol) of lithium hydroxide and 50 ml of THF were introduced into a round-bottomed flask and the mixture was heated at reflux for twelve hours. It was evaporated to dryness, the residue was taken up in water, acidified to pH 1 and extracted with ethyl ether. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica, eluted with ethyl ether. 420 mg (54%) of 4-[3-hydroxy-3-[3-1-adamantyl)-2,4-di(methoxyethoxymethoxy)phenyl]-1-propynyl]benzoic acid, having a melting point of 79°-81° C., were recovered.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for twelve hours
  3. customIt was evaporated to dryness
  4. extractionextracted with ethyl ether
  5. customThe organic phase was separated out
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue obtained
  9. customwas purified by chromatography on a column of silica
  10. washeluted with ethyl ether
  11. customwere recovered

Sources & evidence

ORD record
ord-3662e071556e42569365da0e73d8ac19
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

Loading…