Sodium Sulfate → 2-(3-Hydroxypropylthio)thiophene

HRID 231692Notes

Reaction equation

HRID 231692 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH2:10][CH2:11][S:12][C:13]1[S:17][CH:16]=[CH:15][CH:14]=1)(O)=[O:8].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[OH:8][CH2:7][CH2:10][CH2:11][S:12][C:13]1[S:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 139116455-(2-Carboxyethylthio)thiopheneHCID 21226445Aluminium lithium hydride

Product 1

HCID 222924372-(3-Hydroxypropylthio)thiopheneYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of lithium aluminum hydride (20.1 g, 0.53 mol) in THF (125 ml), cooled to 0° C. was added a solution of 5-(2-carboxyethylthio)thiophene (25.0 g, 0.13 mol) in THF (125 ml) dropwise. The mixture was refluxed for 2 hours, cooled to 0° C. and saturated Na2SO4 was added dropwise. The solid was filtered, washed with CHCl3 and the filtrate was concentrated. Water was added to the residue and extracted with CHCl3. Drying and solvent evaporation gave an oily, product (21.7 g, 96%).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperaturecooled to 0° C.
  3. filtrationThe solid was filtered
  4. washwashed with CHCl3
  5. concentrationthe filtrate was concentrated
  6. additionWater was added to the residue
  7. extractionextracted with CHCl3
  8. customDrying
  9. customsolvent evaporation

Sources & evidence

ORD record
ord-47bb9bbd83cf4d7b8090e65ff39cfc15
Source dataset
uspto-grants-1989_07
Patent number
US04847289

Reaction notes

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