Formaldehyde → HCID 23149157, compound

HRID 1983063Notes

Reaction equation

HRID 1983063 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][NH:6][CH:7]=1.[O:15]1CCC[CH2:16]1.C=O.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[OH:15][CH2:16][N:6]1[CH:7]=[C:3]([C:2]([F:1])([F:13])[F:14])[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 2723671Tetrabutylammonium HydroxideHCID 14370786ethyl 4-(trifluoromethyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 23149157HCID 23149157, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

207 mg of 4-trifluoromethyl-3-ethoxycarbonyl-1H-pyrole, 5 ml of tetrahydrofuran and 5 ml of formaldehyde 36% in water were mixed. 0.2 ml of tetrabutylammonium hydroxide 10% in water was added to the mixture at room temperature, followed by stirring at room temperature for 10 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 crude product of 1-hydroxymethyl-4-trifluoromethyl-3-ethoxycarbonyl-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-41697eef351d4108beb6665486b20947
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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