Tetrahydrofuran → 5'-Ethyl-3'-methoxy-4'-methoxymethoxy-1'-acetonaphthone

HRID 260576Notes

Reaction equation

HRID 260576 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([O:17][CH2:18][O:19][CH3:20])=[C:6]([O:15][CH3:16])[CH:7]=[C:8]2[CH:13]=[O:14])[CH3:2].[Cl-].[NH4+].O1CCC[CH2:24]1>C[Li].ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([O:17][CH2:18][O:19][CH3:20])=[C:6]([O:15][CH3:16])[CH:7]=[C:8]2[C:13](=[O:14])[CH3:24])[CH3:2]

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 99705695-Ethyl-3-methoxy-4-methoxymethoxy-1-naphthalenecarbaldehyde

Product 1

HCID 104468145'-Ethyl-3'-methoxy-4'-methoxymethoxy-1'-acetonaphthone

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 178418348HCID 178418348, compoundSolvent

Procedure

2 g of 5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthalenecarbaldehyde was dissolved in 20 ml of absolute tetrahydrofuran, to which 11.5 ml of an ethyl solution of 1.12M methyl lithium was added at -78° C. After 30 minutes, an ammonium chloride aqueous solution was added to the solution and extracted with ethyl acetate. The resultant organic phase was dried with anhydrous magnesium sulfate and the solvent was distilled off to obtain 2.1 g of a brown oily substance. This substance was dissolved in 20 ml of dichloromethane without isolation and purification, to which 30 g of manganese dioxide was added, followed by agitation at room temperature for 20 hours. The insoluble matters were removed by filtration and the filtrate was concentrated, followed by purification by silica gel column chromatography (10% ethyl acetate/hexane) to obtain 1.3 g of the captioned compound as a yellow oily substance.

Workup

  1. additionwas added at -78° C
  2. extractionextracted with ethyl acetate
  3. dry with materialThe resultant organic phase was dried with anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customto obtain 2.1 g of a brown oily substance
  6. additionwas added
  7. waitfollowed by agitation at room temperature for 20 hours
  8. customThe insoluble matters were removed by filtration
  9. concentrationthe filtrate was concentrated
  10. customfollowed by purification by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-72287fba68444eb59fe286c325f0bf02
Source dataset
uspto-grants-1996_06
Patent number
US05527948

Reaction notes

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