Water → HCID 67378209, compound

HRID 1472964Notes

Reaction equation

HRID 1472964 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:32])[CH2:13]1)[C:27]1[CH:26]=[CH:25][C:24]([OH:31])=[CH:23][C:22]=1[CH2:21][CH2:20]3)(=O)C.O>CCO>[OH:31][C:24]1[CH:25]=[CH:26][C:27]2[C@@H:28]3[C@H:19]([C@H:18]4[C@@:15]([CH2:30][CH2:29]3)([CH2:16][CH3:17])[C:14](=[O:32])[CH:13]=[CH:12]4)[CH2:20][CH2:21][C:22]=2[CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 89586118HCID 89586118, compound

Product 1

HCID 67378209HCID 67378209, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (0.5 ml, 3.6 mmol) was added to a suspension of 15α-acetoxy-3-hydroxy-18-methyl-estra-1,3,5(10)-trien-17-one (0.52 g, 1.5 mmol) in EtOH (7 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 to afford pure 3-hydroxy-18-methyl-estra-1,3,5(10),15-tetraen-17-one (0.27 g, yield: 64%).

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

Sources & evidence

ORD record
ord-e75c258f605646f0a31e41ae9e40cbc2
Source dataset
uspto-grants-2015_04
Patent number
US09012667B2

Reaction notes

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