Diazomethane → HCID 54415567, compound

HRID 2231160Notes

Reaction equation

HRID 2231160 reaction equation
[C:1]([C:3]([C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[N+:13]([O-:15])=[O:14])[OH:5])#[N:2].[N+](=[CH2:24])=[N-]>C1COCC1>[C:1]([C:3]([C:16](=[O:21])[C:17]([CH3:18])([CH3:20])[CH3:19])=[C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[N+:13]([O-:15])=[O:14])[O:5][CH3:24])#[N:2]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 183149Pentanenitrile, 2-[(4-chloro-2-nitrophenyl)hydroxymethylene]-4,4-dimethyl-3-oxo-

Product 1

HCID 54415567HCID 54415567, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.0 g of 2-cyano-4,4-dimethyl-1-hydroxy-3-oxo-(2-nitro-4-chlorophenyl)-1-pentene dissolved in 3 ml of dry THF was cautiously added an ethereal solution of diazomethane. The excess starting material was removed by washing the reaction mixture with cold 3% K2CO3, separating the phases, drying the organic phase over MgSO4, filtering, and concentrating under reduced pressure. The crude product was crystallized from hot hexane/THF to yield 250 mg of the product, m.p. 130°-1° C.

Workup

  1. customwas removed
  2. washby washing the reaction mixture with cold 3% K2CO3
  3. customseparating the phases
  4. dry with materialdrying the organic phase over MgSO4
  5. filtrationfiltering
  6. concentrationconcentrating under reduced pressure
  7. customThe crude product was crystallized from hot hexane/THF

Sources & evidence

ORD record
ord-9aa37d39f7024960acfc9a6bc6fc82dd
Source dataset
uspto-grants-1988_11
Patent number
US04781750

Reaction notes

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