Water → HCID 19976910, compound

HRID 1440345Notes

Reaction equation

HRID 1440345 reaction equation
[C:1]1([C:7]2[CH:11]=[CH:10][S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH2:12].C(Cl)(Cl)Cl>O1CCCC1>[C:1]1([C:7]2[CH:11]=[C:10]([CH:6]([OH:12])[CH2:1][CH2:2][CH3:3])[S:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6212ChloroformHCID 5950443-Phenylisothiazole

Product 1

HCID 19976910HCID 19976910, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolved in 60 ml of anhydrous tetrahydrofuran were 3.1 g (19.1 mmol) of 3-phenylisothiazole, followed by the addition 18.2 ml of an n-butyl lithium-hexane solution (1.57 mol/l) under a nitrogen gas stream at -78° C. over a dry ice-acetone bath. After the resulting mixture was stirred for 1 hour, 1.51 g (21 mmol) of butylaldehyde were added dropwise. The solution was stirred for 1 hour at the same temperature, whereby the reaction was completed. Water and chloroform were added. The reaction product was extracted into an organic layer. The organic layer was concentrated and the concentrate was purified by silica gel chromatography (eluent: 20:1 n-hexane/ethyl acetate), so that 3-phenyl-5-(1-hydroxybutyl)isothiazole was obtained as yellow oil.

Workup

  1. additionfollowed by the addition 18.2 ml of an n-butyl lithium-hexane solution (1.57 mol/l) under a nitrogen gas stream at -78° C. over a dry ice-acetone bath
  2. stirringThe solution was stirred for 1 hour at the same temperature, whereby the reaction
  3. extractionThe reaction product was extracted into an organic layer
  4. concentrationThe organic layer was concentrated
  5. customthe concentrate was purified by silica gel chromatography (eluent: 20:1 n-hexane/ethyl acetate), so that 3-phenyl-5-(1-hydroxybutyl)isothiazole
  6. customwas obtained as yellow oil

Sources & evidence

ORD record
ord-07d828cba11343a18701207cbf0d4754
Source dataset
uspto-grants-1996_03
Patent number
US05498619

Reaction notes

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