Ethyl Acetate → HCID 57169364, compound

HRID 1728514Notes

Reaction equation

HRID 1728514 reaction equation
[CH3:1][C@H:2]([C@@H:5]([O:7][CH:8]1[CH2:13][CH2:12][CH2:11]CO1)C)[CH2:3][OH:4].[CH2:14](I)CCC.[H-].[Na+].C(OCC)(=O)C>CN(C)C=O>[CH2:8]([O:7][CH2:5][C@H:2]([CH3:1])[C@@H:3]([OH:4])[CH3:14])[CH2:13][CH2:12][CH3:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 14656877HCID 14656877, compound

Product 1

HCID 57169364HCID 57169364, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 40 ml of N,N-dimethylformamide were dissolved 5.0 g of the (2S,3S)-2-methyl-3-(2-tetrahydropyranyloxy)butanol obtained in Example 1 i) and 24.5 g of butyl iodide. Thereto was added 1.22 g of oily sodium hydride (about 60%) in small portions with ice-cooling. The mixture was stirred for 2 hours with ice-cooling. The reaction mixture was poured into 300 ml of ethyl acetate and the resulting mixture was stirred. The insoluble materials were removed by filtration. The filtrate was washed with water three times. The organic layer was dried and concentrated. The residue, i.e. crude (2S,3S)-4-butoxy-3-methyl-2-(2-tetrahydropyranyloxy)butane was dissolved in 150 ml of methanol. To the solution was added 6.0 g of a nonaqueous strongly acidic cation exchange resin (Amberlist 15), and the mixture was stirred for 6 hours at room temperature. The cation exchange resin used was removed by filtration and the filtrate was concentrated. The residue was subjected to Kugelrohr distillation under reduced pressure to obtain 2.54 g of (2S, 3S )-4-butoxy-3-methyl-2-butanol.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe resulting mixture was stirred
  4. customThe insoluble materials were removed by filtration
  5. washThe filtrate was washed with water three times
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. dissolutionThe residue, i.e. crude (2S,3S)-4-butoxy-3-methyl-2-(2-tetrahydropyranyloxy)butane was dissolved in 150 ml of methanol
  9. additionTo the solution was added 6.0 g of a nonaqueous strongly acidic cation exchange resin (Amberlist 15)
  10. stirringthe mixture was stirred for 6 hours at room temperature
  11. customThe cation exchange resin used was removed by filtration
  12. concentrationthe filtrate was concentrated
  13. distillationThe residue was subjected to Kugelrohr distillation under reduced pressure

Sources & evidence

ORD record
ord-b074bf7d07684fca9f03ac686e802041
Source dataset
uspto-grants-1994_07
Patent number
US05328643

Reaction notes

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