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

HRID 1875257ノート

反応式

HRID 1875257 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e17fd821062a44b7879422ee08f7e60b
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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