Reaktion #64081

ord-4e34792d8ffc4b14a0fc392c6f7938d8

Reaktionsgleichung

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

Edukte

—
( 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

Reagenzien

Keine

Lösungsmittel

O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionether extraction
  2. 2
    TrocknenAfter 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

Vorschrift

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##

Quelle

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