2,3-Dihydroxybutanedioic Acid → HCID 86749515, compound

HRID 440725Notes

Reaction equation

HRID 440725 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C@H:7]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[CH:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH:15]3OCC[O:26][CH:16]32)[CH2:8]1)C.C(O)(=O)C(C(C(O)=O)O)O.O>O1CCOCC1>[CH:4]([CH2:5][O:6][C@H:7]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[CH:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH2:15][C:16]2=[O:26])[CH2:8]1)=[O:3]

Participants

5

Reactant 3

HCID 8752,3-Dihydroxybutanedioic AcidHCID 962WaterHCID 86749516HCID 86749516, compound

Product 1

HCID 86749515HCID 86749515, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 7.2 g of 3β-(2,2-diethoxyethoxy)-17-ethylenedioxy-androstane, in 250 ml of dioxane and 250 ml of a saturated solution of tartaric acid was heated at 70° C. for 2 hrs in a nitrogen atmosphere, 100 ml of water were then added and the residue was extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using as eluant n-hexane/ethyl acetate 70/30 to give 4.5 g of 3β-formylmethoxy-androstan-17-one as a white solid.

Workup

  1. additionwere then added
  2. extractionthe residue was extracted with methylene chloride
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe crude product was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-b6cfd10e4ae540c99c4d52767e53deb8
Source dataset
uspto-grants-1996_05
Patent number
US05521167

Reaction notes

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