Water → HCID 70231137, compound

HRID 1460662Notes

Reaction equation

HRID 1460662 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])=[CH:10][O:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][C@@H:16]([C:20]([OH:22])=[O:21])[CH2:15]2)=[C:5]([CH3:30])[CH:4]=1.[OH-].[Na+].O>C(O)C>[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])=[CH:10][O:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]=[C:16]([C:20]([OH:22])=[O:21])[CH2:15]2)=[C:5]([CH3:30])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 70230373HCID 70230373, compound

Product 1

HCID 70231137HCID 70231137, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[2-[[2-(4-Fluoro-2-methylphenyl)-2-(2-methyl-phenyl)ethenyl]oxy]ethyl]-1,2,5,6-tetrahydro-3-pyridine carboxylic acid methyl ester (0.74 g, 0.0018 mol) (prepared as described in Method C) was dissolved in ethanol (15 ml) and 10N sodium hydroxide solution (1.8 ml) was introduced. After stirring the reaction mixture for 2 h at room temperature TLC indicated that saponification was incomplete, so further 10 N sodium hydroxide solution (1.8 ml) was added, and the reaction mixture was heated for 10 min. at 40° C. Water (400 ml) was added, and the solution was extracted with diethyl ether (100 ml). The aqueous layer was acidified to pH 5 with 2N hydrochloric acid solution and extracted with dichloromethane (4×50 ml). The combined extracts were dried (MgSO4) and evaporated to a residue (0.61 g) which was dissolved in toluene (50 ml). Methanol (0.2 ml) and chlorotrimethylsilane (0.216 ml) were added, and after mixing, a layer of cyclohexane (ca. 30 ml) was added. After storing this mixture at 4° for 18 h, the title compound was collected by filtration (0.60 g, 77%), m.p. 190°-201° (after drying in vacuo).

Workup

  1. temperaturethe reaction mixture was heated for 10 min. at 40° C
  2. extractionthe solution was extracted with diethyl ether (100 ml)
  3. extractionextracted with dichloromethane (4×50 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated to a residue (0.61 g) which
  6. dissolutionwas dissolved in toluene (50 ml)
  7. additionMethanol (0.2 ml) and chlorotrimethylsilane (0.216 ml) were added
  8. additionafter mixing
  9. additiona layer of cyclohexane (ca. 30 ml) was added
  10. customat 4°
  11. customfor 18 h
  12. filtrationthe title compound was collected by filtration (0.60 g, 77%), m.p. 190°-201° (after drying in vacuo)

Sources & evidence

ORD record
ord-581f7b0ccfab4b2ea0864cfc76a9acc0
Source dataset
uspto-grants-1991_12
Patent number
US05071859

Reaction notes

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