Reacción #64084

ord-e524e68b961847e189e32cc1fcedfdbf

Ecuación de reacción

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 (2R, 3S)-2-methyl-3-hydroxybutanoate

Reactantes

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

Reactivos

Ninguno

Disolventes

O
water

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónether extraction
  2. 2
    SecadoThe ether phase was dried over anhydrous sodium sulfate and ether
  3. 3
    workup.DISTILLATIONwas distilled off
  4. 4
    workup.DISTILLATIONby distilling the residue

Procedimiento

To 1.0 g of (2S, 5S,6S)-2-trichloromethyl-5,6-dimethyl-1,3-dioxan-4-one produced by a 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 to effect ether extraction. The ether phase was dried over anhydrous sodium sulfate and ether was distilled off followed by distilling the residue to obtain 0.4 g of isopropyl (2R, 3S)-2-methyl-3-hydroxybutanoate of the following formula. ##STR61## (2) Repeating the procedure of Example 5-(1) except that 2-propanol was replaced with 2-butanol, 0.5 g of 1-methylpropyl (2R, 3S)-2-methyl-3-hydroxybutanoate of the following formula was obtained.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05411877uspto-grants-1995_05