Sulfuric acid magnesium salt (1:1) → HCID 53681393, compound

HRID 371448Notes

Reaction equation

HRID 371448 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:12][C:11]2[CH2:13][C@@H:14]([O:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[C@H:15]([CH2:16][OH:17])[C:10]=2[CH:9]=1.C([O-])(=O)C.[Na+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl.CCOCC.N1C=CC=CC=1.C(O)(C)C>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:12][C:11]2[CH2:13][C@@H:14]([O:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[C@H:15]([CH:16]=[O:17])[C:10]=2[CH:9]=1

Participants

9

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 517045Sodium AcetateHCID 13216467HCID 13216467, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 53681393HCID 53681393, compoundYield 55.4%

Reagents, catalysts & solvents 4

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 590 mg of the alcohol prepared in Example 13 in 75 ml of methylene chloride is combined with 271 mg of sodium acetate and 534 mg of pyridinium chlorochromate, and the mixture is stirred under argon for 50 minutes. The mixture is combined with a solution of 0.25 ml of isopropanol and 0.5 ml of pyridine in 50 ml of ether and further stirred for 10 minutes. Subsequently 7.5 g of magnesium sulfate is introduced, the reaction solution is filtered, and the residue is washed with ether. The organic solution is applied directly to a 30 g silica gel column and eluted with a hexane/8% acetone-hexane gradient, thus obtaining 325 mg of the title compound as an oil.

Workup

  1. stirringfurther stirred for 10 minutes
  2. filtrationthe reaction solution is filtered
  3. washthe residue is washed with ether
  4. washeluted with a hexane/8% acetone-hexane gradient

Sources & evidence

ORD record
ord-d0eff45d19634e45a8947798d92f8e36
Source dataset
uspto-grants-1985_07
Patent number
US04532236

Reaction notes

Loading…