Water → (+/-)-alpha-(Naphthylthioethyl)-3-pyridinepropanol

HRID 1600894Notes

Reaction equation

HRID 1600894 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][C:9](=[O:23])[CH2:10][CH2:11][S:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)[CH:2]=1.[BH4-].[Na+].O>C(O)C>[C:13]1([S:12][CH2:11][CH2:10][CH:9]([OH:23])[CH2:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:14]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21830630HCID 21830630, compound

Product 1

HCID 21830650(+/-)-alpha-(Naphthylthioethyl)-3-pyridinepropanolYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(3-Pyridyl)-5-(2-naphthylthio)-3-pentanone (0.142 g) and sodium borohydride (0.025 g) were dissolved in ethanol (20 ml) and stirred for 15 hours at room temperature. Water was added to the reaction mixture, which was extracted with dichloromethane, the extracts dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane:ethyl acetate (1:3) to give the title compound as a white solid (0.040 g).

Workup

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

Sources & evidence

ORD record
ord-4665d07dd28c44ff864a3a9f385db622
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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