Hydrochloric Acid → HCID 19812449, compound

HRID 373383Notes

Reaction equation

HRID 373383 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:18]1[C:23]([CH3:24])=[C:22]([C:25](=[O:30])[CH2:26][CH2:27][CH2:28][CH3:29])[C:21]([CH3:31])=[C:20]([CH3:32])[C:19]=1[O:33]C)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]C)=[O:15].N1C(C)=CC(C)=CC=1C.[I-].[Li+].Cl>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:18]1[C:23]([CH3:24])=[C:22]([C:25](=[O:30])[CH2:26][CH2:27][CH2:28][CH3:29])[C:21]([CH3:31])=[C:20]([CH3:32])[C:19]=1[OH:33])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 79532,4,6-TrimethylpyridineHCID 66321Lithium iodideHCID 19812453HCID 19812453, compound

Product 1

HCID 19812449HCID 19812449, compoundYield 46.2%

Procedure

A mixture of methyl 7-(fluorophenyl)-7-(2-methoxy-3,4,6-trimethyl-5-valerylphenyl)heptanoate (0.23 g), collidine (0.38 ml) and lithium iodide (0.2 g) was refluxed for 18 hours. After allowing to cool, the mixture was acidified with addition of lN hydrochloric acid and extracted with ethyl acetate. The organic layer was washed in turn with lN hydrochloric acid, water and saturated saline and dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 7-(fluorophenyl)-7-(2-hydroxy-3,4,6-trimethyl-5-valerylphenyl)heptanoic acid (0.1 g) (Compound 36). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Workup

  1. temperaturewas refluxed for 18 hours
  2. temperatureto cool
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed in turn with lN hydrochloric acid, water and saturated saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5840db9c141c43c297367ae95074bf79
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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