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

HRID 251220노트

반응식

HRID 251220 반응식
[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]

참가 물질

8

반응물 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178433277HCID 178433277, 화합물

생성물 1

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

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-51d4e3180cf246d09cad876904474b10
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863293B2

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