Sodium Acetate → HCID 86759644, compound

HRID 1815785Notes

Reaction equation

HRID 1815785 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@H:12]([CH2:21][OH:22])[CH2:11][CH2:10]4)[C@H:7]([CH3:23])[CH2:6][C:5]=2[CH:4]=1.C([O-])(=O)C.[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@H:12]([CH:21]=[O:22])[CH2:11][CH2:10]4)[C@H:7]([CH3:23])[CH2:6][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 69788141HCID 69788141, compound

Product 1

HCID 86759644HCID 86759644, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

—Pyridinium chlorochromate (10.1 g) was added to a solution of (7α,14β,17α)-3-methoxy-7-methylestra-1,3,5(10)-triene-17-methanol (Example 4, step iv; 5.90 g) in dichloromethane (295 ml) containing sodium acetate (8.85 g) and silica (17.7 g). After 3 h stirring at room temperature the reaction mixture was filtered over dicalite and the filtrate was concentrated under reduced pressure. Column chromatography afforded (7α,14β,17α)-3-methoxy-7-methylestra-1,3,5(10)-triene-17-carboxaldehyde (4.16 g).

Workup

  1. filtrationwas filtered over dicalite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3112a6bc922341168ae4f6d3b12930f1
Source dataset
uspto-grants-2005_04
Patent number
US06881728B1

Reaction notes

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