Ethanol → HCID 19890444, compound

HRID 1031841Notes

Reaction equation

HRID 1031841 reaction equation
C(O)C.[CH2:4]([O:11][C:12]1[C:13]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:14][C:15]([N+:23]([O-])=O)=[C:16]([CH:22]=1)[CH:17]=[CH:18][N+]([O-])=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>[Fe].C(O)(=O)C>[CH2:4]([O:11][C:12]1[CH:22]=[C:16]2[C:15](=[CH:14][C:13]=1[O:26][CH2:27][CH2:28][CH2:29][CH3:30])[NH:23][CH:18]=[CH:17]2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 53681969HCID 53681969, compound

Product 1

HCID 19890444HCID 19890444, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

8.6 g of activated iron are added at 60° C. to a solution of 28 ml of absolute ethanol and 14 ml of acetic acid. The mixture is kept for 15 minutes at 80° C. and 5-benzyloxy-4-butoxy-2,β-dinitrostyrene (1.6 g; 0.0043 mole) is added. The mixture is left at 80° C. for 1 hour, and the ferric sludge is filtered off and rinsed with 40 ml of ethanol and 40 ml of acetic acid. The filtrate is diluted with 100 ml of ice-cold water. After extraction of the solution with methylene chloride and drying of the organic phase over sodium sulphate, the organic phase is concentrated and chromatographed on silica 60 (eluent: toluene/CH2Cl2, 50:50). 0.5 g (40% yield) of the derivative 22 is obtained.

Workup

  1. waitThe mixture is left at 80° C. for 1 hour
  2. filtrationthe ferric sludge is filtered off
  3. washrinsed with 40 ml of ethanol and 40 ml of acetic acid
  4. additionThe filtrate is diluted with 100 ml of ice-cold water
  5. extractionAfter extraction of the solution with methylene chloride
  6. dry with materialdrying of the organic phase over sodium sulphate
  7. concentrationthe organic phase is concentrated
  8. customchromatographed on silica 60 (eluent: toluene/CH2Cl2, 50:50)
  9. custom0.5 g (40% yield) of the derivative 22 is obtained

Sources & evidence

ORD record
ord-edfae5514de545fb9f91f01dc25b3909
Source dataset
uspto-grants-1990_09
Patent number
US04956174

Reaction notes

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