Tetrahydrofuran → Ethyl 5-bromo-4-(hydroxymethyl)-1-phenyl-1H-pyrazole-3-carboxlate

HRID 1521848Notes

Reaction equation

HRID 1521848 reaction equation
[Br:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:3]=1[CH:18]=[O:19].C1COCC1.[BH4-].[Na+]>CCO>[Br:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:3]=1[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 86670903Ethyl 5-bromo-4-formyl-1-phenyl-1H-pyrazole-3-carboxylate

Product 1

HCID 66579973Ethyl 5-bromo-4-(hydroxymethyl)-1-phenyl-1H-pyrazole-3-carboxlateYield 75.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice cooled solution of ethyl 5-bromo-4-formyl-1-phenyl-1H-pyrazole-3-carboxylate (3.82 g, 11.86 mmol, 1 eq) in a 1:1 mixture of THF: EtOH is added sodium borohydride (0.5 g, 13.04 mmol, 1.1 eq) portion wise. The reaction mixture is stirred at RT for 2 h. The reaction mixture is quenched with sat. NH4Cl solution and extracted with EtOAc. The organic layer is dried over Na2SO4 and concentrated. The crude is purified by column chromatography to afford 2.91 g (75%) of the title compound. 1H NMR (DMSO-d6, 400 MHz): δ 7.60-7.56 (m, 5H), 4.95 (t, J=5.4 Hz, 1H), 4.60-4.58 (d, J=5.4 Hz, 2H), 4.32 (q, J=7.01 Hz, 2H), 1.30 (t, J=7.7 Hz, 3H). HPLC (max plot) 96.75%; Rt 3.69 min

Workup

  1. customThe reaction mixture is quenched with sat. NH4Cl solution
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude is purified by column chromatography

Sources & evidence

ORD record
ord-31e5485ad1524d6196e15ecbc37a15dc
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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