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

HRID 1106227Notes

Reaction equation

HRID 1106227 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 54510284HCID 54510284, compoundYield 112.6%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-421d03c19199422b9270c6cf4d7faa52
Source dataset
uspto-grants-1982_01
Patent number
US04312812

Reaction notes

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