Reaction #64083

ord-185c52e8bb324c2f9801394e75d52aba

Reaction equation

C[C@@H]1O[C@H](C(Cl)(Cl)Cl)OC(=O)[C@H]1C
(2S, 5S, 6S)-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, 3S)-2-methyl-3-hydroxybutanoate

Reactants

C[C@@H]1O[C@H](C(Cl)(Cl)Cl)OC(=O)[C@H]1C
(2S, 5S, 6S)-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
  3. 3
    workup.DISTILLATIONthe residue was subjected to distillation

Procedure

To 1.0 g of (2S, 5S, 6S)-2-trichloromethyl-5,6-dimethyl-1,3-dioxan-4-one obtained by procedure similar to Example 1-(7) 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 the residue was subjected to distillation to give 0.4 g of isopropyl (2S, 3S)-2-methyl-3-hydroxybutanoate of the following formula. ##STR51##

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05411877uspto-grants-1995_05