Water → HCID 67369411, compound

HRID 1472965Notes

Reaction equation

HRID 1472965 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]([Cl:32])[CH2:20]3)(=O)C.O>C(O)C>[Cl: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 89284210HCID 89284210, compound

Product 1

HCID 67369411HCID 67369411, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

Triethylamine (0.5 ml, 3.6 mmol) was added to a suspension of 15α-acetoxy-6-chloro-18-methyl-estra-4-en-3,17-dione (0.5 g, 1.32 mmol) in ethanol (15 ml). The mixture was stirred at 45° C. for 2 h, cooled to 10° C. and water (4 ml) was then added. The precipitate was filtered and washed with an ethanol/water (1/1) mixture. The crude product was crystallized from ethanol and dried under vacuum to afford 6-chloro-18-methyl-estra-4,15-dien-3,17-dione (0.26 g, yield: 62%).

Workup

  1. temperaturecooled to 10° C.
  2. filtrationThe precipitate was filtered
  3. washwashed with an ethanol/water (1/1) mixture
  4. customThe crude product was crystallized from ethanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-b654d3110a664d1d9d9df75551e27918
Source dataset
uspto-grants-2015_04
Patent number
US09012667B2

Reaction notes

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