Hydrochloric Acid → 9-Hydroxypregn-4-ene-3,20-dione

HRID 1613982ノート

反応式

HRID 1613982 の反応式
[N+](C(=[C:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@:19]([OH:24])([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12]([CH2:13][C:14]4(OCC[O:25]4)[CH2:15][CH2:16]2)=[CH:11][CH2:10]3)[CH2:7][CH2:6]1)C)#[C-].Cl.O.[CH2:31]([O:33]CC)[CH3:32]>O1CCCC1.[OH-].[Na+]>[OH:24][C@:19]12[CH2:9][CH2:8][C@@:22]3([CH3:23])[C@@H:21]([CH2:7][CH2:6][C@@H:5]3[C:31](=[O:33])[CH3:32])[C@@H:20]1[CH2:10][CH2:11][C:12]1[C@:17]2([CH3:18])[CH2:16][CH2:15][C:14](=[O:25])[CH:13]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 5698545720-Isocyano-3,3-ethylenedioxypregna-5,17(20)-dien-9alpha-ol

生成物 1

HCID 131887039-Hydroxypregn-4-ene-3,20-dione

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

A solution of 20-isocyano-3,3-ethylenedioxypregna-5,17(20)-dien-9α-ol (2.30 g) in a mixture of tetrahydrofuran (60 ml) and aqueous 2N hydrochloric acid (20 ml) was refluxed for 1 hour. The reaction mixture was cooled to room temperature after which water (25 ml) and diethyl ether (100 ml) were added. The mixture was neutralised with IN sodium hydroxide solution. After separating the layers the aqueous phase was extracted twice with diethyl ether (50 ml). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to afford 2.02 g of the title compound.

後処理

  1. temperaturewas refluxed for 1 hour
  2. additionwere added
  3. customAfter separating the layers the aqueous phase
  4. extractionwas extracted twice with diethyl ether (50 ml)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f13ac462c06a4fdbb78aed308a551fdd
出典データセット
uspto-grants-1993_03
特許番号
US05194602

反応ノート

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