Ethanol → HCID 12805914, compound

HRID 904062Notes

Reaction equation

HRID 904062 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH:11]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)[C:12]([CH3:17])([N+:14]([O-])=O)[CH3:13])=[CH:5][CH:4]=1.C(O)C>[Zn].C(O)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH:11]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[C:12]([CH3:17])([CH3:13])[N:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 128059131-(4-Methoxyphenyl)-4-methyl-4-nitro-3-(thiophen-2-yl)pentan-1-one

Product 1

HCID 12805914HCID 12805914, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 284Formic AcidSolvent

Procedure

180 G. of zinc powder are added portionwise while stirring over a period of 5 hours to a solution of 194 g. of 4'-methoxy-4-methyl-4-nitro-3-(2-thienyl)-valerophenone in 400 ml. of ethanol and 400 ml. of formic acid. The temperature is held at 48°-50° C. during this addition. The zinc sludge is then filtered off and the filtrate strongly concentrated under reduced pressure. The residue is taken up in water and made alkaline with 3-N sodium hydroxide. The mixture is extracted with methylene chloride, the organic phase washed with water, dried over sodium sulfate and evaporated under reduced pressure. The oily residue is chromatographed on silica gel, elution being carried out firstly with pure benzene and then with benzene/acetone mixtures with increasing acetone content (up to 50% acetone). There is obtained 2-(p-methoxy-phenyl)-5,5-dimethyl-4-(2-thienyl)-1-pyrroline which melts at 84° C. after recrystallization from n-hexane.

Workup

  1. additionThe temperature is held at 48°-50° C. during this addition
  2. filtrationThe zinc sludge is then filtered off
  3. concentrationthe filtrate strongly concentrated under reduced pressure
  4. extractionThe mixture is extracted with methylene chloride
  5. washthe organic phase washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe oily residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-eec0c7f020024e05b08c33e4e942494e
Source dataset
uspto-grants-1980_10
Patent number
US04230623

Reaction notes

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