Diisopropylethylamine → [5-Methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-methanol

HRID 1592629ノート

反応式

HRID 1592629 の反応式
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[CH2:7][OH:8].CCN(C(C)C)C(C)C.[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23]Cl>CN(C=O)C.[Cl-].[Na+].O.O.CCOC(C)=O>[CH3:1][C:2]1[N:3]([CH2:23][O:22][CH2:21][CH2:20][Si:19]([CH3:26])([CH3:25])[CH3:18])[CH:4]=[N:5][C:6]=1[CH2:7][OH:8]

参加物

8

反応物 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178433277HCID 178433277、化合物

生成物 1

HCID 67271606[5-Methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-methanol収率 56%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a stirred solution of 4-methyl-5-imidazolemethanol (587 mg, 3.96 mmol) in anhydrous DMF (13 mL) was added DIPEA (2.1 mL, 11.9 mmol) followed by 2-(trimethylsilyl)ethoxymethyl chloride (793 mg, 4.76 mmol). The resultant solution was heated to 80° C. for 3 h then cooled to room temperature. The reaction mixture was poured into brine (15 mL), and diluted with H2O (6 mL) and EtOAc (40 mL). The phases were mixed vigorously for 10 minutes and separated. The organic phase was washed with brine (4×20 mL), dried (Na2SO4), and concentrated under reduced pressure. Purification of the crude orange oil by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 95:4:1) provided [5-Methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-methanol (535 mg, 56%) as a mixture of regioisomers.

後処理

  1. additionThe phases were mixed vigorously for 10 minutes
  2. customseparated
  3. washThe organic phase was washed with brine (4×20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the crude orange oil by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 95:4:1)

出典と根拠

ORDレコード
ord-1c81c638e602464596832787842e8b27
出典データセット
uspto-grants-2007_11
特許番号
US07291631B2

反応ノート

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