Sodium borohydride → [4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazol-5-yl]methanol

HRID 1875257Notes

Reaction equation

HRID 1875257 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:5]=[CH:6][N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:8]=1[CH:9]=[O:10]>CO>[Cl:3][C:4]1[N:5]=[CH:6][N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:8]=1[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 715339724-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carbaldehyde

Product 1

HCID 70937149[4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazol-5-yl]methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.37 g, 9.78 mmol) was added to a 0° C. solution of 4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carbaldehyde (1.70 g, 6.52 mmol) in methanol (26 ml). Gas evolution was observed and the reaction mixture was stirred at RT for 30 mins and evaporated. Sat'd NaHCO3 and CH2Cl2 were added to the residue and the aqueous layer was extracted with CH2Cl2 (4×20 mL). The combined organic phase was dried (Na2SO4), filtered and evaporated to give [4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazol-5-yl]methanol as a light yellow oil. A solution of this alcohol, imidazole (0.89 g, 13.0 mmol) and TBSCI (1.47 g, 9.78 mmol) in CH2Cl2 (22 mL) was stirred at RT overnight. Sat'd NaHCO3 was added and the aqueous layer was extracted with CH2Cl2 (2×20 mL). The combined organic phase was dried (Na2SO4), filtered, evaporated and purified by silica gel chromatography (0-35% EtOAc/hexanes) to give the title compound (2.19 g, 89%) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.44 (s, 1H), 5.35 (s, 2H), 4.72 (s, 2H), 3.51 (t, J=8.2 Hz, 2H), 0.90-0.96 (m, 2H), 0.89 (s, 9H), 0.09 (s, 6H), 0.00 (s, 9H).

Workup

  1. customevaporated
  2. additionSat'd NaHCO3 and CH2Cl2 were added to the residue
  3. extractionthe aqueous layer was extracted with CH2Cl2 (4×20 mL)
  4. dry with materialThe combined organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e17fd821062a44b7879422ee08f7e60b
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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