Diethyl Ether → HCID 18509486, compound

HRID 1356843Notes

Reaction equation

HRID 1356843 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[C:22]([C:26]1[CH:45]=[CH:44][C:29]([CH2:30][N:31]([CH2:33][C:34]2[CH:35]=[C:36]([CH:40]([OH:43])[CH2:41][CH3:42])[CH:37]=[CH:38][CH:39]=2)[CH3:32])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].C(OCC)C.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[C:22]([C:26]1[CH:45]=[CH:44][C:29]([CH2:30][N:31]([CH2:33][C:34]2[CH:35]=[C:36]([C:40](=[O:43])[CH2:41][CH3:42])[CH:37]=[CH:38][CH:39]=2)[CH3:32])=[CH:28][CH:27]=1)([CH3:23])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24083Sulfuric acid magnesium salt (1:1)HCID 2724130Cornforth reagentHCID 18509424HCID 18509424, compound

Product 1

HCID 18509486HCID 18509486, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium dichromate (2.89 g; 7.68 mmol) was suspended in methylene chloride (30 ml). While the suspension was stirred at room temperature, Compound 92 (0.50 g; 1.54 mmol) in methylene chloride (5 ml) was added dropwise. The mixture was stirred for 4 hours, and diethyl ether (30 ml) and magnesium sulfate (3 g) were added thereto, followed by stirring for 10 minutes. Insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to thereby yield 0.19 g of the target compound as colorless transparent oily matter (yield: 38.1%).

Workup

  1. stirringThe mixture was stirred for 4 hours
  2. stirringby stirring for 10 minutes
  3. filtrationInsoluble matter was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-1f91a15240254da596f1dbbc41eeeb4c
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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