Water → HCID 45264916, compound

HRID 249447Notes

Reaction equation

HRID 249447 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][CH:15]=[C:16]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[CH3:32])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[CH3:24])[CH2:7]1)=[O:5])C.[OH-].[Na+].O.[Cl:36][Si](C)(C)C>C(O)C.C1(C)C=CC=CC=1.CO>[ClH:36].[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[CH3:24])=[CH:15][O:14][CH2:13][CH2:12][N:8]2[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]2)=[C:26]([CH3:32])[CH:27]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 10528708HCID 10528708, compound

Product 1

HCID 45264916HCID 45264916, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

(R)-1-[2-[[2,2-bis(4-Fluoro-2-methylphenyl)ethenyl]oxy]-ethyl]-3-piperidine carboxylic acid ethyl ester (1.72 g, 0.0039 mol) (prepared as described in Method D) was dissolved in ethanol (20 ml) and 10 N sodium hydroxide solution (4 ml) was introduced. The solution was stirred at room temperature for 3 h and water (100 ml) was added. The solution was extracted with diethyl ether (2 × 100 ml) and the aqueous phase was acidified to pH 5 with 2 N hydrochloric acid solution. Extraction with dichloromethane (4 × 80 ml) and drying of the combined extracts (MgSO4) followed by evaporation gave a residue, which was dissolved in toluene (50 ml). Methanol (0.16 ml) and chlorotrimethylsilane (0.51 ml) were added, and the product precipitated. The mixture was evaporated to a solid and recrystallized from toluene to give the title compound as a white crystalline solid (0.78 g, 44%), m.p. 175°-185° (decomp.)

Workup

  1. extractionThe solution was extracted with diethyl ether (2 × 100 ml)
  2. extractionExtraction with dichloromethane (4 × 80 ml)
  3. dry with materialdrying of the combined extracts (MgSO4)
  4. customfollowed by evaporation
  5. customgave a residue, which
  6. customthe product precipitated
  7. customThe mixture was evaporated to a solid
  8. customrecrystallized from toluene

Sources & evidence

ORD record
ord-38fef08f8c5340cc8b16a7ee413b3c0b
Source dataset
uspto-grants-1993_05
Patent number
US05214057

Reaction notes

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