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Barium thiocyanate → 3alpha-Hydroxy-21-thiocyanato-5alpha-pregnane-11,20-dione

HRID 1077010
ノート
印刷プレビュー

反応式

HRID 1077010 の反応式
Br[CH2:2][C:3](=[O:25])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C@H:13]([OH:24])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.[S-:26][C:27]#[N:28].[Ba+2].[S-]C#N>CC(C)=O.O>[OH:24][C@@H:13]1[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[C:19](=[O:23])[CH2:20][C@@:21]2([CH3:22])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:3](=[O:25])[CH2:2][S:26][C:27]#[N:28])[CH2:12]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 164928Barium thiocyanateHCID 8673346721-Bromo-3alpha-hydroxy-5alpha-pregnane-11,20-dione

生成物 1

HCID 867334693alpha-Hydroxy-21-thiocyanato-5alpha-pregnane-11,20-dione収率 96.4%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

A solution of 21-bromo-3α-hydroxy-5α-pregnane-11,20-dione (0.75 g.) in acetone (50 ml.) was treated with a solution of barium thiocyanate (2.6 g.) in water (10 ml.). The resulting mixture was refluxed for 4 hr., cooled and then partitioned between water and ether. The organic layer was washed with water, dried (Na2SO4) and evaporated. The residue (720 mg.) was purified by preparative t.l.c. (EtOAc) to afford title compound (685 mg.) as a white foam, [α]D + 67°.

後処理

  1. temperatureThe resulting mixture was refluxed for 4 hr
  2. temperature, cooled
  3. custompartitioned between water and ether
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue (720 mg.) was purified by preparative t.l.c

出典と根拠

ORDレコード
ord-f95ae8a8889449b3b1f6a56d6a96519a
出典データセット
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US03959260

反応ノート

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