反応 #93008

ord-63038de424534fef9fb36a0e4480c1ce

反応方程式

O=C(O)CCC1CCCCC1
cyclohexanepropionic acid
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)CBr
16β-ethyl-17β-bromoacetoxy-4-estren-3-one
CN(C)C=O
DMF
→
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)COC(=O)CCC1CCCCC1
above-identified compound
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)COC(=O)CCC1CCCCC1
16β-Ethyl-17β-(3-cyclohexylpropionyl)oxyacetoxy-4-estren-3-one

反応物

O=C(O)CCC1CCCCC1
cyclohexanepropionic acid
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)CBr
16β-ethyl-17β-bromoacetoxy-4-estren-3-one
CN(C)C=O
DMF

試薬

なし

溶媒

CC(C)=O
acetone
[Na+].[OH-]
NaOH

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    workup.ADDITIONis added
  2. 2
    温度The mixture is refluxed for 8 hours
  3. 3
    workup.ADDITIONtreated in the same manner as Example 26
  4. 4
    その他The reaction mixture is chromatographed on a silica gel column
  5. 5
    洗浄passage of 200 ml of n-hexane-diisopropyl ether (3:7), elution
  6. 6
    workup.ADDITIONis carried out with 800 ml of a 1:1 mixture of the same solvents
  7. 7
    その他The eluate is evaporated under reduced pressure
  8. 8
    その他to remove the solvent

実験手順

In 20 ml of acetone is dissolved 1.0 ml of cyclohexanepropionic acid, and 3.0 ml of 2N-NaOH is added, followed by addition of 1.2 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 20 ml of DMF. The mixture is refluxed for 8 hours, and thereafter treated in the same manner as Example 26. The reaction mixture is chromatographed on a silica gel column. Following passage of 200 ml of n-hexane-diisopropyl ether (3:7), elution is carried out with 800 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.21 g of the above-identified compound as a light-yellow viscous oil.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US04609650uspto-grants-1986_09