Ethyl orthoformate → HCID 67362053, compound

HRID 1472948Notes

Reaction equation

HRID 1472948 reaction equation
C(OCC)(OCC)O[CH2:3][CH3:4].[C:11]([O:14][C@@H:15]1[C@H:21]2[C@H:22]3[C@H:31]([CH2:32][CH2:33][C@:18]2([CH2:19][CH3:20])[C:17](=[O:35])[CH2:16]1)[C@@H:30]1[C:25](=[CH:26][C:27](=[O:34])[CH2:28][CH2:29]1)[CH2:24][CH2:23]3)(=[O:13])[CH3:12]>CCO.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:11]([O:14][C@@H:15]1[C@H:21]2[C@H:22]3[C@H:31]([CH2:32][CH2:33][C@:18]2([CH2:19][CH3:20])[C:17](=[O:35])[CH2:16]1)[C@@H:30]1[C:25]([CH:26]=[C:27]([O:34][CH2:3][CH3:4])[CH2:28][CH2:29]1)=[CH:24][CH2:23]3)(=[O:13])[CH3:12]

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 67361589HCID 67361589, compound

Product 1

HCID 67362053HCID 67362053, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolvent

Procedure

Triethyl orthoformate (30 ml, 180 mmol) and p-Toluenesulfonic acid (300 mg, 1.57 mmol) were added to a suspension of 15α-acetoxy-18-methyl-estr-4-en-3,17-dione (30 g, 87 mmol) in EtOH (180 ml). The mixture was stirred at room temperature for 1 h, and then cooled to 0° C. The precipitate was filtered, washed with cooled ethanol and dried under vacuum to afford 15α-acetoxy-3-ethoxy-18-methyl-estra-3,5-dien-17-one (31.5 g, yield: 97%).

Workup

  1. temperaturecooled to 0° C
  2. filtrationThe precipitate was filtered
  3. washwashed with cooled ethanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-3ba8a172e94546c0a5e44fd874bb9193
Source dataset
uspto-grants-2015_04
Patent number
US09012667B2

Reaction notes

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