Water → HCID 45095564, compound

HRID 916694Notes

Reaction equation

HRID 916694 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[N:6]([CH2:17][CH3:18])[N:5]=1.C(O)(C(F)(F)F)=O.O>C1COCC1>[CH2:17]([N:6]1[C:7]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[CH:8][C:4]([CH:3]=[O:2])=[N:5]1)[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 58757369HCID 58757369, compound

Product 1

HCID 45095564HCID 45095564, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(3-dimethoxymethyl-1-ethyl-1H-pyrazol-5-yl)-benzonitrile (5.0 g, 18.4 mmol), TFA (5.0 mL), H2O (20 mL) and THF (50 mL) was stirred at RT for 1 hour and then concentrated under reduced pressure to remove the organic solvents. The residue was neutralised with 1N NaOH solution (100 mL), extracted with EtOAc (2×150 mL), dried (MgSO4) and concentrated under reduced pressure while dry loading onto MgSO4. The mixture was then purified by column chromatography on silica eluting with 35-60% EtOAc/iso-hexanes to yield the desired aldehyde (2.91 g, 70%). 1H NMR (CDCl3, 500 MHz) δ 10.00 (1H, s), 7.80-7.72 (1H, m), 7.70 (1H, s), 7.67-7.60 (2H, m), 6.84 (1H, s), 4.23 (2H, q, J=7.3 Hz), 1.49 (3H, t, J=7.3 Hz). MS (ES+) C13H11N3O requires: 225, found: 226 (M+H+, 100%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the organic solvents
  3. extractionextracted with EtOAc (2×150 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customwhile dry loading onto MgSO4
  7. customThe mixture was then purified by column chromatography on silica eluting with 35-60% EtOAc/iso-hexanes

Sources & evidence

ORD record
ord-1dd26d6d09f1407197e93d9fa6e42ad9
Source dataset
uspto-grants-2007_09
Patent number
US07271191B2

Reaction notes

Loading…