Sulfuric Acid → HCID 22941791, compound

HRID 650334Notes

Reaction equation

HRID 650334 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C@@H:19]1[C:14](=[CH:15][C:16](=[O:23])[CH2:17][CH2:18]1)[CH2:13][C@H:12]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][Si](C(C)(C)C)(C)C)(=[O:3])[CH3:2].S(=O)(=O)(O)O>CO.C(OCC)C>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C@@H:19]1[C:14](=[CH:15][C:16](=[O:23])[CH2:17][CH2:18]1)[CH2:13][C@H:12]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 57126443HCID 57126443, compound

Product 1

HCID 22941791HCID 22941791, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 48 g of 17β-acetoxy-7α-(5-tert-butyldimethylsilyloxypentyl)-estr-4-en-3-one in 350 ml of methanol is allowed to stand with 35 ml of 8 vol % sulfuric acid for 30 minutes at room temperature. The solution is diluted with diethyl ether, washed neutral with water, and dried. After the concentration by evaporation, 37.7 g of 17β-acetoxy-7α-(5-hydroxypentyl)-estr-4-en-3-one is obtained as oil.

Workup

  1. customfor 30 minutes
  2. customat room temperature
  3. washwashed neutral with water
  4. customdried
  5. concentrationAfter the concentration
  6. customby evaporation

Sources & evidence

ORD record
ord-0401bebac7704e1b9c31abea98572f58
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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