Ethanol → 21-Ethoxymethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 1973721Notes

Reaction equation

HRID 1973721 reaction equation
[OH:1][C@@H:2]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:19]2[C:18](=[O:24])[CH2:17][C@@:16]2([CH3:25])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:15])[CH:13]=[CH2:14])[CH2:3]1.C(=O)(O)[O-].[K+].O.[CH2:32]([OH:34])[CH3:33]>>[CH2:32]([O:34][CH2:14][CH2:13][C:12](=[O:15])[C@@H:11]1[C@:16]2([CH3:25])[C@H:8]([C@H:7]3[C@H:19]([C:18](=[O:24])[CH2:17]2)[C@:20]2([CH3:23])[C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:22][CH2:21]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1)[CH3:33]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 516893Potassium BicarbonateHCID 86734286HCID 86734286, compound

Product 1

HCID 8673428821-Ethoxymethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Procedure

3α-Hydroxy-21-methylene-5α-pregnane11,20 -dione (250 mg) was dissolved in ethanol (50 ml) and potassium bicarbonate solution (10%; 3 ml) added to the refluxing solution. After 3/4 hour the mixture was poured into water, and extracted into ether. The extract was washed with water, dried (Na2SO4) and evaporated to a white solid (190 mg) which was recrystallised from ether to give title compound (120 mg) m.p. 126°-129.5° C [α]D + 87.5° (c, 1.03).

Workup

  1. extractionextracted into ether
  2. washThe extract was washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated to a white solid (190 mg) which
  5. customwas recrystallised from ether

Sources & evidence

ORD record
ord-9cd716a80bb44c7fb66fbf9679ece576
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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