Potassium Hydroxide → HCID 69917394, compound

HRID 1837275Notes

Reaction equation

HRID 1837275 reaction equation
C([O:4][C@@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C:19]2=[O:23])[C@H:15]2[C@H:6]1[C@@H:7]1[C:12]([CH2:13][C@H:14]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][Cl:33])=[CH:11][C:10](=[O:34])[CH2:9][CH2:8]1)(=O)C.[OH-].[K+]>O1CCCC1.CO.C(OCC)(=O)C>[Cl:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C@@H:14]1[CH2:13][C:12]2[C@H:7]([CH2:8][CH2:9][C:10](=[O:34])[CH:11]=2)[C@@H:6]2[C@@H:15]1[C@H:16]1[C@@:20]([CH2:22][C@H:5]2[OH:4])([CH3:21])[C:19](=[O:23])[CH2:18][CH2:17]1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 69916333HCID 69916333, compound

Product 1

HCID 69917394HCID 69917394, compoundYield 58.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

6.0 g of 11α-acetoxy-7α-(9-chlorononyl)-estr-4-ene-3,17-dione is saponified at 60° C. in a mixture of 12 ml of tetrahydrofuran and 12 ml of methanol with 17 ml of a 1N potassium hydroxide solution. After 3 hours, it is diluted with ethyl acetate, washed neutral with saturated sodium chloride solution and water and dried. The chromatography of the crude product on silica gel with a methylene chloride-acetone gradient yields 3.2 g of 7α-(9-chlorononyl)-11α-hydroxy-estr-4-ene-3,17-dione as an oil.

Workup

  1. washwashed neutral with saturated sodium chloride solution and water
  2. customdried

Sources & evidence

ORD record
ord-43f411418c01476c8b8a926d80f4e094
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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