1-Butyne, 3-(1-ethoxyethoxy)-3-methyl- → HCID 54510284、化合物

HRID 1106227ノート

反応式

HRID 1106227 の反応式
[CH2:1]([O:3][CH:4]([O:6][C:7]([CH3:11])([CH3:10])[C:8]#[CH:9])[CH3:5])[CH3:2].C([Li])CCC.[CH2:17]([O:19][CH:20]([O:22][C@@H:23]1[C@@:53]2([CH3:54])[C:27](=[CH:28][CH2:29][C@@H:30]3[C@@H:52]2[CH2:51][CH2:50][C@@:49]2([CH3:55])[C@H:31]3[CH2:32][CH2:33][C@@H:34]2[C@H:35]([CH3:48])[CH2:36]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:26][C@@H:25]([O:56][CH:57]([O:59][CH2:60][CH3:61])[CH3:58])[CH2:24]1)[CH3:21])[CH3:18]>O1CCOCC1.CCCCCC>[CH2:17]([O:19][CH:20]([O:22][C@@H:23]1[C@@:53]2([CH3:54])[C:27](=[CH:28][CH2:29][C@@H:30]3[C@@H:52]2[CH2:51][CH2:50][C@@:49]2([CH3:55])[C@H:31]3[CH2:32][CH2:33][C@@H:34]2[C@H:35]([CH3:36])[CH2:48][C:9]#[C:8][C:7]([O:6][CH:4]([O:3][CH2:1][CH3:2])[CH3:5])([CH3:11])[CH3:10])[CH2:26][C@@H:25]([O:56][CH:57]([O:59][CH2:60][CH3:61])[CH3:58])[CH2:24]1)[CH3:21])[CH3:18]

参加物

6

反応物 3

HCID 122013871-Butyne, 3-(1-ethoxyethoxy)-3-methyl-HCID 56981575HCID 56981575、化合物HCID 178418339Butyllithium

生成物 1

HCID 54510284HCID 54510284、化合物収率 112.6%

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

A stirred solution, cooled to 9° C., of 46.8 g (0.3 mol) of 3-(1-ethoxyethoxy)-3-methyl-but-1-yne in 1.0 liters of dioxane was treated dropwise under argon with 150 ml (0.3 mol) of 2M n-butyl lithium in hexane. The solution was stirred at 7°-9° C. for 2 hours and at room temperature for 2 hours. Thereafter, there was added to the mixture a solution of 67.0 g of (20S)-1α,3β-bis(1-ethoxyethoxy)-20-methyl-21-(p-toluenesulphonyloxy)-pregn-5-ene in 0.4 liters of dioxane and, while stirring, solvent was distilled off until the internal temperature was 93° C. The mixture was then stirred at 100° C. under argon for 64 hours. After cooling, carbon dioxide was conducted into the mixture. The mixture was poured into ice water, and the emulsion was extracted with ether. The extracts were washed with saturated sodium chloride solution, dried and evaporated. There were obtained 73.6 g of crude 1α,3β,25-tris(1-ethoxyethoxy)-cholest-5-en-23-yne.

後処理

  1. stirringwhile stirring
  2. distillationsolvent was distilled off until the internal temperature
  3. customwas 93° C
  4. stirringThe mixture was then stirred at 100° C. under argon for 64 hours
  5. temperatureAfter cooling
  6. additionThe mixture was poured into ice water
  7. extractionthe emulsion was extracted with ether
  8. washThe extracts were washed with saturated sodium chloride solution
  9. customdried
  10. customevaporated

出典と根拠

ORDレコード
ord-421d03c19199422b9270c6cf4d7faa52
出典データセット
uspto-grants-1982_01
特許番号
US04312812

反応ノート

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