Reacción #64081

ord-4e34792d8ffc4b14a0fc392c6f7938d8

Ecuación de reacción

C[C@H]1O[C@@H](C(Cl)(Cl)Cl)OC(=O)[C@@H]1C
(2R, 5R, 6R)-2-trichloromethyl-5,6-dimethyl-1,3-dioxan-4-one
O=S(=O)(O)O
sulfuric acid
CC(C)O
2-propanol
→
CC(C)OC(=O)[C@H](C)[C@@H](C)O
isopropyl (2R, 3R)-2-methyl-3-hydroxybutanoate

Reactantes

—
( 1)-(4 )
C[C@H]1O[C@@H](C(Cl)(Cl)Cl)OC(=O)[C@@H]1C
(2R, 5R, 6R)-2-trichloromethyl-5,6-dimethyl-1,3-dioxan-4-one
O=S(=O)(O)O
sulfuric acid
CC(C)O
2-propanol

Reactivos

Ninguno

Disolventes

O
water

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónether extraction
  2. 2
    SecadoAfter drying the ether phase over anhydrous sodium sulfate
  3. 3
    workup.DISTILLATIONthe ether was distilled off
  4. 4
    workup.DISTILLATIONthe residue was subjected to distillation

Procedimiento

To 1.0 g of (2R, 5R, 6R)-2-trichloromethyl-5,6-dimethyl-1,3-dioxan-4-one obtained by procedures similar to (1)-(4) of Example 1 were added 0.1 ml of concentrated sulfuric acid and 10 ml of 2-propanol and stirred at room temperature for one hour, and 20 ml of water was added to effect ether extraction. After drying the ether phase over anhydrous sodium sulfate, the ether was distilled off and the residue was subjected to distillation to give 0.4 g of isopropyl (2R, 3R)-2-methyl-3-hydroxybutanoate. The NMR chart is shown in FIG. 6. ##STR31##

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05411877uspto-grants-1995_05