Water → 3beta-(2,2-Diethoxy-ethoxy)-17beta-(3-furyl)-5beta-androstan-14beta-ol

HRID 233636Notes

Reaction equation

HRID 233636 reaction equation
[H-].[Na+].[O:3]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@:11]3([OH:28])[C@H:14]4[C@H:24]([CH2:25][CH2:26][C@:9]23[CH3:10])[C@:22]2([CH3:23])[C@@H:17]([CH2:18][C@@H:19]([OH:27])[CH2:20][CH2:21]2)[CH2:16][CH2:15]4)=[CH:4]1.[CH2:29]([O:31][CH:32]([O:35][CH2:36][CH3:37])[CH2:33]Br)[CH3:30].O>O1CCCC1>[CH2:29]([O:31][CH:32]([O:35][CH2:36][CH3:37])[CH2:33][O:27][C@H:19]1[CH2:20][CH2:21][C@@:22]2([CH3:23])[C@H:17]([CH2:16][CH2:15][C@@H:14]3[C@@H:24]2[CH2:25][CH2:26][C@@:9]2([CH3:10])[C@:11]3([OH:28])[CH2:12][CH2:13][C@@H:8]2[C:5]2[CH:6]=[CH:7][O:3][CH:4]=2)[CH2:18]1)[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 1606964617beta-(3-Furyl)-5beta,14beta-androstane-3beta,14beta-diol

Product 1

HCID 700467603beta-(2,2-Diethoxy-ethoxy)-17beta-(3-furyl)-5beta-androstan-14beta-ol

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 7.0 g of 17β-(3-furyl)-5β-androstane-3β,14β-diol (II-a: Ref. comp.) (Minato H. and Nagasaki T., J. Chem. Soc.(C), 1966, 377) were added at room temperature in a nitrogen atmosphere. The mixture was kept at reflux for 6 hrs, then 26 ml of bromoacetaldehyde diethylacetal were added; the suspension was kept at reflux 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 6.9 g of 3β-(2,2-diethoxy-ethoxy)-17β-(3-furyl)-5β-androstan-14β-ol, as a dense oil.

Workup

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

Sources & evidence

ORD record
ord-bd19f50832c04ff49647a3a9a97042bb
Source dataset
uspto-grants-1997_01
Patent number
US05593982

Reaction notes

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