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

HRID 1647626ノート

反応式

HRID 1647626 の反応式
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]

参加物

5

反応物 3

HCID 962WaterHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 131719038(3-Furyl)-5beta-androstane-3beta,14beta-diol

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b6464555c95945bda6a2f20697b4695b
出典データセット
uspto-grants-1995_07
特許番号
US05432169

反応ノート

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