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

HRID 1077010
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HRID 1077010 반응식
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
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-f95ae8a8889449b3b1f6a56d6a96519a
출처 데이터셋
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US03959260

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