Hydrochloric Acid → HCID 86733300, compound

HRID 1606365Notes

Reaction equation

HRID 1606365 reaction equation
[C:1]([CH2:3][CH2:4][O:5][C@H:6]1[CH2:25][C@@:24]2([CH3:26])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:23]2[C:22](=[O:27])[CH2:21][C@@:20]2([CH3:28])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:19])[CH3:18])[CH2:8][C@@H:7]1[OH:29])#N.Cl.[OH2:31].[CH2:32]([OH:34])[CH3:33]>>[CH2:32]([O:34][C:1]([CH2:3][CH2:4][O:5][C@H:6]1[CH2:25][C@@:24]2([CH3:26])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:23]2[C:22](=[O:27])[CH2:21][C@@:20]2([CH3:28])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:19])[CH3:18])[CH2:8][C@@H:7]1[OH:29])=[O:31])[CH3:33]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 86733299HCID 86733299, compound

Product 1

HCID 86733300HCID 86733300, compound

Procedure

2β-(2-Cyanoethoxy)-3α-hydroxy-5α-pregnane-11,20-dione (430 mg.) was dissolved in absolute ethanol (50 ml) and dry hydrogen chloride passed through the solution until saturation occurred. The mixture was left for one-fourth hour then poured into water (250 ml.). After one-half hour the precipitate formed was extracted into ether (2 × 100 ml), the ethereal solution washed with water and dried over anhydrous sodium sulphate. The dried solution was evaporated to a white form (320 mg) which was purified by preparative T.L.C. using ethyl acetate/petrol (4/1) run twice. The main band (Rf[0.4) gave title compound (140 mg) as an oil. [α]D + 61°(c, 0.5%).

Workup

  1. waitThe mixture was left for one-fourth hour
  2. customAfter one-half hour the precipitate formed
  3. extractionwas extracted into ether (2 × 100 ml)
  4. washthe ethereal solution washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customThe dried solution was evaporated to a white form (320 mg) which
  7. customwas purified by preparative T.L.C

Sources & evidence

ORD record
ord-569b6631c8074683bb37b7317d6e3b52
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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