Réaction #64081

ord-4e34792d8ffc4b14a0fc392c6f7938d8

Équation de réaction

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

Réactifs

—
( 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

Réactifs

Aucun

Solvants

O
water

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Extractionether extraction
  2. 2
    SéchageAfter 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

Mode opératoire

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##

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05411877uspto-grants-1995_05