Acetone → HCID 53921069, compound

HRID 1248615Notes

Reaction equation

HRID 1248615 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=3)[C:10]([OH:24])([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[CH2:9]2)=[CH:4][CH:3]=1.Br[CH2:26][C:27]([O:29]CC)=[O:28].[CH3:32][C:33](C)=O>>[CH2:32]([N:21]1[CH2:20][CH:19]=[C:18]([C:10]2([OH:24])[C:11]3[C:16](=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=3)[CH:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:9]2)[CH2:23][CH:22]1[CH2:26][C:27]([OH:29])=[O:28])[CH3:33]

Participants

4

Reactant 3

HCID 180AcetoneHCID 7748Ethyl bromoacetateHCID 20277025HCID 20277025, compound

Product 1

HCID 53921069HCID 53921069, compoundYield 92.7%

Procedure

3-(4'-fluorophenyl)-1-hyroxy-6-methyl-1-pyrid-4-ylindane (12.0 g) was refluxed with ethyl bromoacetate (7.5 g) in acetone (100 ml) for 4 hrs. The reaction mixture was cooled in a refrigerator over night and the precipitate filtered off. Yield: 16.8 g (91.9%) of the pyridiniumbromide. MP: 196°-198° C. (dec.). The bromide (15.0 g) was dissolved in methanol (150 ml), and ice cooled, NaBH4 (5.0 g) was added during a period of 1 h. The reaction mixture was finally stirred for another 1/2 h at room temperature and subsequently poured into NH4Cl (25 g) in 1 L of H2O. The H2O phase was extracted with ethyl acetate (2×200 ml), the combined organic phases dried (MgSO4) and the solvent evaporated yielding 11.7 g (92.7%) of 1-(1-ethylcarboxymethyl-1,2,3,6-tetrahydropyrid-4-yl)-3-(4'-fluorphenyl)-1-hydroxy-6-methylindane. MP: 119° -20° C.

Workup

  1. temperatureThe reaction mixture was cooled in a refrigerator over night
  2. filtrationthe precipitate filtered off
  3. dissolutionThe bromide (15.0 g) was dissolved in methanol (150 ml)
  4. temperatureice cooled
  5. additionNaBH4 (5.0 g) was added during a period of 1 h
  6. additionsubsequently poured into NH4Cl (25 g) in 1 L of H2O
  7. extractionThe H2O phase was extracted with ethyl acetate (2×200 ml)
  8. dry with materialthe combined organic phases dried (MgSO4)
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-0288089174024ee093e8f1cba978da6e
Source dataset
uspto-grants-1985_06
Patent number
US04525360

Reaction notes

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