Formaldehyde → HCID 23149123, compound

HRID 1983059Notes

Reaction equation

HRID 1983059 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][CH:5]=1)([O-:3])=[O:2].[O:9]1CCC[CH2:10]1.C=O.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[OH:9][CH2:10][N:6]1[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 1458133-NitropyrroleHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 23149123HCID 23149123, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

840 mg of 3-nitro-1H-pyrole, 15 ml of tetrahydrofuran and 15 ml of formaldehyde 36% in water were mixed. 0.5 ml of tetrabutylammonium hydroxide 10% in water was added at room temperature, followed by stirring at room temperature for 30 minutes. The reaction mixture was poured into ice-water, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain 1-hydroxymethyl-3-nitro-1H-pyrole.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e5f9ae82b2ca49c7bde615fe40820983
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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