Sulfuric Acid → HCID 69916490, compound

HRID 1837273Notes

Reaction equation

HRID 1837273 reaction equation
[C:1]([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][O:33][Si](C(C)(C)C)(C)C)=[CH:11][C:10](=[O:41])[CH2:9][CH2:8]1)(=[O:3])[CH3:2].S(=O)(=O)(O)O>CO.C(OCC)(=O)C>[C:1]([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][OH:33])=[CH:11][C:10](=[O:41])[CH2:9][CH2:8]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 57063157HCID 57063157, compound

Product 1

HCID 69916490HCID 69916490, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

19.9 g of 11α-acetoxy-7α-(9-tert-butyldimethylsilyloxynonyl)-estr-4-ene-3,17-dione in 90 ml of methanol is mixed at room temperature with 20 ml of 8% sulfuric acid. After 2.5 hours, it is diluted with ethyl acetate, washed neutral with saturated sodium bicarbonate solution and water and dried. The chromatography of the crude product on silica gel with a methylene chloride-acetone gradient yields 15.8 g of 11α-acetoxy-7α-(9-hydroxynonyl)-estr-4-ene-3,17-dione as a foam.

Workup

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

Sources & evidence

ORD record
ord-cf0c6563ee5f407bb9a59be880e6e71d
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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