Water → HCID 67368697, compound

HRID 1472963Notes

Reaction equation

HRID 1472963 reaction equation
C(N(CC)CC)C.C(O[C@@H:12]1[C@H:18]2[C@H:19]3[C@H:28]([CH2:29][CH2:30][C@:15]2([CH2:16][CH3:17])[C:14](=[O:33])[CH2:13]1)[C@@H:27]1[C:22](=[CH:23][C:24](=[O:31])[CH2:25][CH2:26]1)[CH:21]([OH:32])[CH2:20]3)(=O)C.O>CCO>[OH:32][CH:21]1[C:22]2[C@H:27]([CH2:26][CH2:25][C:24](=[O:31])[CH:23]=2)[C@@H:28]2[C@H:19]([C@H:18]3[C@@:15]([CH2:30][CH2:29]2)([CH2:16][CH3:17])[C:14](=[O:33])[CH:13]=[CH:12]3)[CH2:20]1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 67370071HCID 67370071, compound

Product 1

HCID 67368697HCID 67368697, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (0.5 ml, 3.6 mmol) was added to a suspension of 15α-acetoxy-6-hydroxy-18-methyl-estr-4-en-3,17-dione (0.5 g, 1.4 mmol) in EtOH (3 ml). The mixture was heated under reflux for 2 h, cooled to room temperature and then water (30 ml) was added. The mixture was extracted with ethyl acetate (30 ml), the organic layer was washed with water (50 ml), dried and the solvent removed. The crude product was purified by flash chromatography on silica gel eluting with diisopropyl ether/ethyl acetate (7/3) to afford pure 6-hydroxy-18-methyl-estra-4,15-dien-3,17-dione (0.14 g, yield: 34%) as an oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. extractionThe mixture was extracted with ethyl acetate (30 ml)
  4. washthe organic layer was washed with water (50 ml)
  5. customdried
  6. customthe solvent removed
  7. customThe crude product was purified by flash chromatography on silica gel eluting with diisopropyl ether/ethyl acetate (7/3)

Sources & evidence

ORD record
ord-23594e44eb8a44a68d951083e5bb5dda
Source dataset
uspto-grants-2015_04
Patent number
US09012667B2

Reaction notes

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