Реакция #64083

ord-185c52e8bb324c2f9801394e75d52aba

Уравнение реакции

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

Реактанты

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

Реагенты

Нет

Растворители

O
water

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

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

Методика

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##

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05411877uspto-grants-1995_05