Water → (+/-)-alpha-(2-Naphthylthiomethyl)-3-pyridinepropanol

HRID 1600887Notes

Reaction equation

HRID 1600887 reaction equation
[H-].[Na+].[CH:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([SH:13])[CH:9]=[CH:10]2)=[CH:5][CH:4]=1.[O:14]1[CH2:16][CH:15]1[CH2:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.O>CN(C)C=O.O1CCCC1>[CH:7]1[C:6]2[C:11](=[CH:12][CH:3]=[CH:4][CH:5]=2)[CH:10]=[CH:9][C:8]=1[S:13][CH2:16][CH:15]([OH:14])[CH2:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 70582-NaphthalenethiolHCID 24758Sodium hydrideHCID 10877288HCID 10877288, compound

Product 1

HCID 9883138(+/-)-alpha-(2-Naphthylthiomethyl)-3-pyridinepropanolYield 48.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil, 0.05 g) was added to a solution of 2-thionaphthol (0.174 g) in dry dimethylformamide (3 ml). A solution of (±)-3-(2-oxiranylethyl)pyridine (0.15 g) in tetrahydrofuran (1 ml) was added and the reaction mixture stirred for three hours at ambient temperature. The solution was poured into water which was extracted with ethyl acetate. The organic extracts were separated, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The product was purified by column chromatography on silica eluting with ethyl acetate to give the title compound as a white solid (0.15 g).

Workup

  1. extractionwas extracted with ethyl acetate
  2. customThe organic extracts were separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by column chromatography on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-42d7c5bd4382410da56a858c7167f1b3
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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