反応 #93007

ord-82d35332a58445748650ceff7a8713cd

反応方程式

O=C(O)C1CCCCC1
cyclohexanecarboxylic acid
[Na+].[OH-]
NaOH
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)C1CCCCC1
above-identified compound
収率 88.2%
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)C1CCCCC1
16β-Ethyl-17β-cyclohexanecarbonyloxyacetoxy-4-estren-3-one
収率 88.2%

反応物

O=C(O)C1CCCCC1
cyclohexanecarboxylic acid
[Na+].[OH-]
NaOH
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

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    温度The mixture is refluxed for 5 hours
  2. 2
    workup.ADDITIONtreated in the same manner as Example 26
  3. 3
    その他The reaction mixture is then chromatographed on a silica gel column
  4. 4
    洗浄passage of 200 ml of n-hexane-diisopropyl ether (6:4), elution
  5. 5
    workup.ADDITIONis carried out with 600 ml of a 1:1 mixture of the same solvents
  6. 6
    その他The eluate is evaporated under reduced pressure
  7. 7
    その他to remove the solvent

実験手順

In 20 ml of acetone is dissolved 0.64 g of cyclohexanecarboxylic acid, and 2.5 ml of 2N-NaOH and then 1.0 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 20 ml of DMF are serially added to the above solution. The mixture is refluxed for 5 hours, and thereafter treated in the same manner as Example 26. The reaction mixture is then chromatographed on a silica gel column. Following passage of 200 ml of n-hexane-diisopropyl ether (6:4), elution is carried out with 600 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 0.98 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