反応 #1049574

ord-f35b277aa025424781d64a28bcb251ba

反応方程式

C[C@@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O)CC[C@]5(C)[C@H]4[C@@H](Br)C(=O)[C@]3(C)[C@H]1[C@@H]2C
(3β,5α,11β,25R)-11-bromospirostan-3-ol-12-one
CC(C)(C)O
t-butanol
[Na+].[OH-]
sodium hydroxide
→
C[C@@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O)CC[C@]5(C)[C@H]4C(=O)[C@@H](O)[C@]3(C)[C@H]1[C@@H]2C
(3β,5α,12β,25R)spirostan-3,12-diol-11-one

反応物

C[C@@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O)CC[C@]5(C)[C@H]4[C@@H](Br)C(=O)[C@]3(C)[C@H]1[C@@H]2C
(3β,5α,11β,25R)-11-bromospirostan-3-ol-12-one
CC(C)(C)O
t-butanol
[Na+].[OH-]
sodium hydroxide

試薬

なし

溶媒

O
water

反応条件

温度
83°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    温度The reaction was heated
  2. 2
    温度to reflux over 1.5 hours
  3. 3
    温度maintained
  4. 4
    温度cooled to room temperature
  5. 5
    その他reaction

実験手順

A glass lined reactor was charged with 12.4 Kg of (3β,5α,11β,25R)-11-bromospirostan-3-ol-12-one (24.34 mole), 33 gallons of t-butanol, 33 gallons of water and 7.5 Kg (189 mole, 7.75 eq) of sodium hydroxide pellets. The reaction was heated to reflux over 1.5 hours, maintained at reflux for 4.5 hours (pot temperature was 83° C.), then cooled to room temperature. TLC at this point indicated complete reaction.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05760009uspto-grants-1998_06