Acetylacetone → 21-(2', 2'-Diacetylethyl)-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 1973718Notes

Reaction equation

HRID 1973718 reaction equation
[O-]CC.[Na+].[Na].[C:6]([CH2:9][C:10](=[O:12])[CH3:11])(=[O:8])[CH3:7].[OH:13][C@@H:14]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:16]([CH2:17][CH2:18][C@@H:19]3[C@@H:31]2[C:30](=[O:36])[CH2:29][C@@:28]2([CH3:37])[C@H:20]3[CH2:21][CH2:22][C@@H:23]2[C:24](=[O:27])[CH:25]=[CH2:26])[CH2:15]1>C(O)C.O>[C:6]([CH:9]([C:10](=[O:12])[CH3:11])[CH2:26][CH2:25][C:24](=[O:27])[C@@H:23]1[C@:28]2([CH3:37])[C@H:20]([C@H:19]3[C@H:31]([C:30](=[O:36])[CH2:29]2)[C@:32]2([CH3:35])[C@H:16]([CH2:15][C@H:14]([OH:13])[CH2:34][CH2:33]2)[CH2:17][CH2:18]3)[CH2:21][CH2:22]1)(=[O:8])[CH3:7]

Participants

7

Reactant 4

HCID 31261AcetylacetoneHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 86734286HCID 86734286, compound

Product 1

HCID 8673428521-(2', 2'-Diacetylethyl)-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of sodium ethoxide, prepared from 120 mg of sodium in ethanol (20 ml), was treated with acetylacetone (1 ml) and the resulting solution added to a solution of 3α-hydroxy-21-methylene-5α-pregnane-11,20-dione (500 mg) in ethanol (20 ml). The mixture was stirred at room temperature for 1 hour, poured into water, and extracted into ether. The extract was washed with water, dried (Na2SO4) and evaporated to a white foam which was purified by preparative t.l.c. (ethyl acetate/petrol) to give title compound (480 mg) as a white foam [α]D + 79.5 °(c, 0.59).

Workup

  1. extractionextracted into ether
  2. washThe extract was washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated to a white foam which
  5. customwas purified by preparative t.l.c

Sources & evidence

ORD record
ord-52b26e4431434ae69edff18f47bbaf37
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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