1-Butyne, 3-(1-ethoxyethoxy)-3-methyl- → HCID 54510284, 화합물

HRID 1106227노트

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HRID 1106227 반응식
[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]

참가 물질

6

반응물 3

HCID 122013871-Butyne, 3-(1-ethoxyethoxy)-3-methyl-HCID 56981575HCID 56981575, 화합물HCID 178418339Butyllithium

생성물 1

HCID 54510284HCID 54510284, 화합물수율 112.6%

시약·촉매·용매 2

HCID 8058Hexane용매HCID 312751,4-Dioxane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-421d03c19199422b9270c6cf4d7faa52
출처 데이터셋
uspto-grants-1982_01
특허 번호
US04312812

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