Ethyl Acetate → HCID 57158131, compound

HRID 2253565

Reaction equation

HRID 2253565 reaction equation
[OH:1][C@@H:2]([CH3:10])[C@@H:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].I(O[CH3:15])(=O)=O.[H-].[Na+].C(OCC)(=O)C>CN(C)C=O>[CH3:15][O:1][C@@H:2]([CH3:10])[C@@H:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 642623ethyl-(2R)-methyl-(3S)-hydroxybutanoateHCID 13203471Methyl iodate

Product 1

HCID 57158131HCID 57158131, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl (2R, 3S)-3-hydroxy-2-methylbutyrate (8.20 g) and methyl iodate (78.0 g) were dissolved in N,N-dimethylformamide (150 ml). To this solution was added sodium hydride (about 60% in oil, 2.46 g) little by little with ice cooling and the mixture was stirred for 1 hour with ice cooling. The reaction mixture was poured into ethyl acetate (300 ml) and the mixture was stirred for 10 minutes. Insoluble materials were filtered off and the filtrate was washed 3 times with water. The organic layer was dried, concentrated and distilled under reduced pressure (b.p. 80° C./30 mmHg) to obtain ethyl (2R, 3S)-3-methoxy-2-methylbutyrate (6.87 g).

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. filtrationInsoluble materials were filtered off
  3. washthe filtrate was washed 3 times with water
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. distillationdistilled under reduced pressure (b.p. 80° C./30 mmHg)

Sources & evidence

ORD record
ord-e9b8d2372f61430f882f6799184a0467
Source dataset
uspto-grants-1993_08
Patent number
US05232853

Linked notes

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