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

HRID 1647626Notes

Reaction equation

HRID 1647626 reaction equation
O1C=CC([CH2:6][C@:7]23[CH2:24][CH2:23][C@H:22]4[C@@H:12]([CH2:13][CH2:14][C@H:15]5[C@:20]4([CH3:21])[CH2:19][CH2:18][C@H:17]([OH:25])[CH2:16]5)[C@@:11]2([OH:26])[CH2:10][CH2:9][CH2:8]3)=C1.[CH2:27]([O:29][CH:30]([O:33][CH2:34][CH3:35])[CH2:31]Br)[CH3:28].[OH2:36]>O1CCCC1>[CH2:27]([O:29][CH:30]([O:33][CH2:34][CH3:35])[CH2:31][O:25][C@H:17]1[CH2:18][CH2:19][C@@:20]2([CH3:21])[C@H:15]([CH2:14][CH2:13][C@@H:12]3[C@@H:22]2[CH2:23][CH2:24][C@@:7]2([CH3:6])[C@:11]3([OH:26])[CH2:10][CH2:9][C@@H:8]2[C:7]2[CH:8]=[CH:9][O:36][CH:6]=2)[CH2:16]1)[CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 131719038(3-Furyl)-5beta-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 Nail (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-b6464555c95945bda6a2f20697b4695b
Source dataset
uspto-grants-1995_07
Patent number
US05432169

Reaction notes

Loading…