Reaktion #64083

ord-185c52e8bb324c2f9801394e75d52aba

Reaktionsgleichung

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

Edukte

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

Reagenzien

Keine

Lösungsmittel

O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionfollowed by ether extraction
  2. 2
    TrocknenThe ether phase was dried over anhydrous sodium sulfate
  3. 3
    workup.DISTILLATIONthe residue was subjected to distillation

Vorschrift

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##

Quelle

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