Acetic Acid → (S)-1-trityloxy-2,4-butanediol

HRID 1168054Notes

Reaction equation

HRID 1168054 reaction equation
[OH:1][C@H:2]([CH2:9][O:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:4](OCC)=[O:5].[BH4-].[Na+].C(O)(=O)C>C(O)C.O>[C:11]([O:10][CH2:9][C@@H:2]([OH:1])[CH2:3][CH2:4][OH:5])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 10883658(S)-ethyl 3-hydroxy-4-trityloxybutanoate

Product 1

HCID 14027585(S)-1-trityloxy-2,4-butanediolYield 82.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In ethanol (10 ml) was dissolved (S)-ethyl 3-hydroxy-4-trityloxybutanoate (0.37 g, 0.975 mmol). Sodium borohydride (0.238 g, 6.29 mmol) was added to the solution and the solution was stirred at room temperature over night. Acetic acid was added to neutralize the solution. The solution was diluted with water (100 ml) and extracted with ethyl acetate. The extract was washed with saturated brine, dried on magnesium sulfate, filtered, and condensed in vacuo. The residue was subjected to silica gel chromatography to give (S)-1-trityloxy-2,4-butanediol (0.28 g, yield 82%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. customdried on magnesium sulfate
  4. filtrationfiltered
  5. customcondensed in vacuo

Sources & evidence

ORD record
ord-77054286635e455885abdad53fd3a3b7
Source dataset
uspto-grants-2003_09
Patent number
US06620977B1

Reaction notes

Loading…