Реакция #1173116

ord-2dde5313947f46a090dca57632cbefff

Уравнение реакции

CC(=O)O
acetic acid
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@]32OO4
qinghaosu
[BH4-].[Na+]
sodium borohydride
→
C[C@H]1[C@@H](O)O[C@@H]2OC3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3
Dihydroqinghaosu

Реактанты

CC(=O)O
acetic acid
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@]32OO4
qinghaosu
[BH4-].[Na+]
sodium borohydride

Реагенты

Нет

Растворители

CO
methanol

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Другоеat 0°-5°
  2. 2
    Концентрированиеconcentrated
  3. 3
    workup.ADDITIONdiluted with water
  4. 4
    ДругоеThe white precipitate formed
  5. 5
    Другоеwas collected
  6. 6
    Другоеdried
  7. 7
    ДругоеRecrystallization of the solid from acetone-hexane afforded white needles mp: 153°-58° C., 3.2 g (80)

Методика

To a solution of 4 g (0.014 m) of qinghaosu (I) in 200 ml of methanol, was added 4 g of sodium borohydride in small portions, keeping the reaction mixture at 0°-5°. After stirring for 60 min, the mixture was neutralized with glacial acetic acid, concentrated and diluted with water. The white precipitate formed was collected and dried. Recrystallization of the solid from acetone-hexane afforded white needles mp: 153°-58° C., 3.2 g (80).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05011951uspto-grants-1991_04