Ethanol → HCID 19890444, compound

HRID 620655Notes

Reaction equation

HRID 620655 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 expected derivative 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 expected derivative is obtained

Sources & evidence

ORD record
ord-7a245b2e3a2d470787628c31d0908188
Source dataset
uspto-grants-1989_04
Patent number
US04822375

Reaction notes

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