Sodium Hydroxide → HCID 54549896, compound

HRID 373379Notes

Reaction equation

HRID 373379 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[C:24]([CH3:25])=[C:23]([CH:26]=[CH:27][C:28](=[O:30])[CH3:29])[C:22]([CH3:31])=[C:21]([CH3:32])[C:20]=2[OH:33])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:19]2[C:24]([CH3:25])=[C:23]([CH:26]=[CH:27][C:28](=[O:30])[CH3:29])[C:22]([CH3:31])=[C:21]([CH3:32])[C:20]=2[OH:33])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86746325HCID 86746325, compound

Product 1

HCID 54549896HCID 54549896, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 7-(4-fluorophenyl)-7-[2-hydroxy-5-(3-oxobutenyl)-3,4,6-trimethylphenyl]heptanoate (0.95 g) in tetrahydrofuran (15 ml) was added aqueous 1N sodium hydroxide (5 ml) and the mixture was stirred at room temperature for 15 hours. The solvent was distilled off under reduced pressure and the residue was acidified by addition of 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed in turn with water and saturated saline and dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from acetonitrile to obtain 7-(4-fluorophenyl)-7-[2-hydroxy-5-(3-oxobutenyl)-3,4,6-trimethylphenyl]heptanoic acid (0.85 g) (Compound 41). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionthe residue was acidified by addition of 1N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed in turn with water and saturated saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-dbd0f6764f6d45ed92512350bc36d1d0
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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