反応 #2195516

ord-c35149602ede4a0ca33686c35f7191ca

反応方程式

C[C@]12C=C[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CCC21OCCO1
17,17-ethylenedioxyandrosta-1.5-dien-3β-ol
C[C@]12C=C[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CCC21OCCO1
17,17-ethylenedioxyandrosta-1,5-dien-3β-ol
CC(=O)OC(C)=O
acetic anhydride
→
CC(=O)O[C@H]1C=C[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CCC23OCCO3)C1
3β-acetoxy-17,17-ethylenedioxyandrosta-1,5-diene

反応物

C[C@]12C=C[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CCC21OCCO1
17,17-ethylenedioxyandrosta-1.5-dien-3β-ol
C[C@]12C=C[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CCC21OCCO1
17,17-ethylenedioxyandrosta-1,5-dien-3β-ol
CC(=O)OC(C)=O
acetic anhydride
—
ice water

試薬

なし

溶媒

c1ccncc1
pyridine

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    抽出the compound was extracted with ether
  2. 2
    洗浄The organic layer was washed with ice-water several times
  3. 3
    乾燥dried over anhydrous magnesium sulfate
  4. 4
    その他Evaporation of the solvent in vacuo below 35° C.
  5. 5
    その他gave 1.0 g of crude solid
  6. 6
    その他Recrystallization from methanol

実験手順

A mixture of crude 17,17-ethylenedioxyandrosta-1.5-dien-3β-ol (4, 1.2 g) in pyridine (10 ml) and acetic anhydride (3 ml) was stirred at room temperature for 16 hours. The reaction mixture was poured into ice-water and the compound was extracted with ether. The organic layer was washed with ice-water several times followed by brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent in vacuo below 35° C. gave 1.0 g of crude solid. Recrystallization from methanol gave 3β-acetoxy-17,17-ethylenedioxyandrosta-1,5-diene (5). Mp. 105-6° C.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07514420B2uspto-grants-2009_04