Water → HCID 21830704, compound

HRID 1600892Notes

Reaction equation

HRID 1600892 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][C:13](=[O:22])[CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.[BH4-].[Na+].O>C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH:13]([OH:22])[CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21830730HCID 21830730, compound

Product 1

HCID 21830704HCID 21830704, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(2-Naphthyl)-1-(3-pyridyl)-3-pentanone (0.327 g) and sodium borohydride were dissolved in ethanol (30 ml) and stirred overnight at room temperature. Water was added to the solution and the mixture extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate:dichloromethane (2:1) to yield the title compound as a white solid (0.117 g).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography over silica eluting with ethyl acetate:dichloromethane (2:1)

Sources & evidence

ORD record
ord-b79251f4c38f4039a0d8ffa156841b76
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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