Réaction #64082

ord-200ed0ecda1945e8b1b680337cb3c45e

Équation de réaction

C[C@@H]1C(=O)O[C@H](C(Cl)(Cl)Cl)O[C@@H]1C
(2R, 5S, 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 (2S, 3R)-2-methyl-3-hydroxybutanoate

Réactifs

C[C@@H]1C(=O)O[C@H](C(Cl)(Cl)Cl)O[C@@H]1C
(2R, 5S, 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
    Extractionfollowed by ether extraction
  2. 2
    SéchageThe ether phase was dried over anhydrous sodium sulfate and ether
  3. 3
    workup.DISTILLATIONwas distilled off
  4. 4
    workup.DISTILLATIONthe residue was subjected to distillation

Mode opératoire

To 1.0 g of (2R, 5S, 6R)-2-trichloromethyl-5,6-dimethyl-1,3-dioxan-4-one obtained by procedure similar to Example 1-(4) were added 0.1 ml of concentrated sulfuric acid and 10 ml of 2-propanol, stirred at room temperature for one hour, and 20 ml of water was added followed by ether extraction. The ether phase was dried over anhydrous sodium sulfate and ether was distilled off, and then the residue was subjected to distillation to obtain 0.4 g of isopropyl (2S, 3R)-2-methyl-3-hydroxybutanoate. ##STR41##

Source

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