Reaction #64082

ord-200ed0ecda1945e8b1b680337cb3c45e

Reaction equation

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

Reactants

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

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Extractionfollowed by ether extraction
  2. 2
    DryingThe 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

Procedure

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.v1Patent: US05411877uspto-grants-1995_05