Water → HCID 86733301, compound

HRID 1606366Notes

Reaction equation

HRID 1606366 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:20]([CH3:22])([CH2:21][C@@H:2]12)[C@@H:19]1[C@H:8]([C@H:9]2[C@:16]([CH3:24])([CH2:17][C:18]1=[O:23])[C@@H:12]([C:13](=[O:15])[CH3:14])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.[OH2:25]>C(O)(=O)CC>[OH:25][C@@H:3]1[C@@H:2]([O:1][C:2](=[O:1])[CH2:3][CH3:4])[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[C:18](=[O:23])[CH2:17][C@@:16]2([CH3:24])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:13](=[O:15])[CH3:14])[CH2:4]1

Participants

4

Reactant 2

HCID 962WaterHCID 86733130HCID 86733130, compound

Product 1

HCID 86733301HCID 86733301, compound

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

2α,3α-Epoxy-5α-pregnane-11,20-dione (500 mg) was dissolved in propionic acid (10 ml) and the solution heated on a steam bath for 5 hours. The mixture was poured into water (200 ml) and the white precipitate extracted into ether. The ethereal solution was washed with 2N-sodium hydroxide solution until the aqueous layer remained basic, then water and then dried over anhydrous sodium sulphate. The dried solution was evaporated to a white foam (560 mg) which was purified by preparative T.L.C. using ethyl acetate/petrol (2/1). The main band (Rf 0.4-0.5) gave title compound (393 mg.) as a white foam. [α]D + 84.4° (c 1.05).

Workup

  1. temperaturethe solution heated on a steam bath for 5 hours
  2. extractionthe white precipitate extracted into ether
  3. washThe ethereal solution was washed with 2N-sodium hydroxide solution until the aqueous layer
  4. dry with materialwater and then dried over anhydrous sodium sulphate
  5. customThe dried solution was evaporated to a white foam (560 mg) which
  6. customwas purified by preparative T.L.C

Sources & evidence

ORD record
ord-c466c2b4f9d74be2b2f5d69add8cf98a
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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