Water → HCID 86749516, compound

HRID 440724Notes

Reaction equation

HRID 440724 reaction equation
[H-].[Na+].[CH2:3]1[CH2:12][O:11][CH:10]2[CH:5]([C@:6]3([CH2:25][CH2:24][C@H:23]4[C@@H:13]([CH2:14][CH2:15][CH:16]5[C@:21]4([CH3:22])[CH2:20][CH2:19][C@H:18]([OH:26])[CH2:17]5)[C@@H:8]3[CH2:9]2)[CH3:7])[O:4]1.[CH2:27]([O:29][CH:30]([O:33][CH2:34][CH3:35])[CH2:31]Br)[CH3:28].O>O1CCCC1>[CH2:27]([O:29][CH:30]([O:33][CH2:34][CH3:35])[CH2:31][O:26][C@H:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[CH:16]([CH2:15][CH2:14][C@@H:13]3[C@@H:23]2[CH2:24][CH2:25][C@@:6]2([CH3:7])[C@H:8]3[CH2:9][CH:10]3[O:11][CH2:12][CH2:3][O:4][CH:5]32)[CH2:17]1)[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 86749514HCID 86749514, compound

Product 1

HCID 86749516HCID 86749516, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5.5 g of NaH (60% dispersion in mineral oil) in 400 ml of dry tetrahydrofuran 8.5 g of 17-ethylenedioxy-androstan-3β-ol were added at room temperature under nitrogen atmosphere. The mixture was kept at 40° C. for 2 hrs, then 26 ml of bromoacetaldehyde diethylacetal were added and the suspension was kept at the same temperature for 4 hrs; 50 ml of water were added cautiously, and the tetrahydrofuran was distilled under reduced pressure. The residue was extracted with methylene chloride, the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 80/20 as eluant to give 7.5 g of 3β-(2,2-diethoxyethoxy)-17-ethylenedioxy-androstane as a thick oil.

Workup

  1. additionwere added at room temperature under nitrogen atmosphere
  2. waitthe suspension was kept at the same temperature for 4 hrs
  3. distillationthe tetrahydrofuran was distilled under reduced pressure
  4. extractionThe residue was extracted with methylene chloride
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe crude product was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-c76c76a0672047a99a06dd3d0402e945
Source dataset
uspto-grants-1996_05
Patent number
US05521167

Reaction notes

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