Lithium borohydride → (5-Phenyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-3-yl)methanol

HRID 513179Notes

Reaction equation

HRID 513179 reaction equation
[C:1]1([C:7]2[N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[N:10]=[C:9]([C:20](OC)=[O:21])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[BH4-]>C1COCC1>[C:1]1([C:7]2[N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:18])[CH3:19])[N:10]=[C:9]([CH2:20][OH:21])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 71212623methyl 5-phenyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-3-carboxylate

Product 1

HCID 86720568(5-Phenyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-3-yl)methanolYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 5-phenyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-3-carboxylate (380 mg, 1.143 mmole) in THF (5 mL) was added 2M LiBH4 in THF (0.9 mL, 1.800 mmole) at RT. After 30 min the mixture was heated to reflux. After 45 min the mixture was cooled to RT and quenched by slow addition of 1M NaOH. The mixture was diluted with H2O and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered through a pad of Celite washing with CH2Cl2, and concentrated to give the title compound (327 mg, 94%) as a clear oil. 1H NMR (399 MHz, CDCl3): δ 7.60 (dd, J=7.4, 1.5 Hz, 2 H); 7.48-7.40 (m, 3 H); 6.40 (s, 1 H); 5.38 (s, 2 H); 4.74 (d, J=5.8 Hz, 2 H); 3.76-3.67 (m, 2 H); 2.03-1.96 (m, 1 H); 0.98-0.89 (m, 2 H); 0.01 (s, 9 H).

Workup

  1. temperatureAfter 30 min the mixture was heated to reflux
  2. customquenched by slow addition of 1M NaOH
  3. additionThe mixture was diluted with H2O
  4. extractionextracted with CH2Cl2 (3×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered through a pad of Celite
  7. washwashing with CH2Cl2
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-aa8cd718cd2d45d39a99a175117bf639
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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