Iodoethane → HCID 69693476, 화합물

HRID 967814노트

반응식

HRID 967814 반응식
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:19]=[CH:18]2)=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li][CH2:29][CH2:30]CC.CCCCCC.C(I)C>O1CCCC1.O>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:19]=[C:18]2[CH2:29][CH3:30])=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 6340IodoethaneHCID 8058HexaneHCID 69693088HCID 69693088, 화합물HCID 178418339Butyllithium

생성물 1

HCID 69693476HCID 69693476, 화합물수율 92%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred solution of 1-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]-4-phenyl-1H-imidazole (1.89 g, 5.0 mmol) in tetrahydrofuran (40 mL) was added a solution of 1.5 M n-BuLi in hexane (3.5 mL, 5.5 mmol) at −78° C. over 10 min. After 30 min, a solution of ethyl iodide (2.0 mL, 25.0 mmol) in tetrahydrofuran (10 mL) was added slowly to the mixture at −78° C. The resultant mixture was warmed to room temperature and stirred for 2 h. To the reaction mixture was added water and the volatile components were removed under reduced pressure. The aqueous phase was extracted with ethyl acetate and the combined organic phase was dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 10:1 to 6:1) to afford 1.86 g (92%) of the title compound as pale yellow oil: MS (ESI) m/z 379 [M+H]+1H-NMR (CDCl3)δ0.00 (6H, s), 0.88 (9H, s), 1.26 (3H, t, J=7.5 Hz), 2.73 (2H, q, J=7.5 Hz), 2.91 (2H, t, J=6.6 Hz), 3.89 (2H, t, J=6.6 Hz), 7.22-7.28 (4H, m), 7.33-7.41 (4H, m), 7.81 (2H, d, J=7.1 Hz).

후처리

  1. customthe volatile components were removed under reduced pressure
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined organic phase was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 10:1 to 6:1)

출처 및 근거

ORD 기록
ord-30c91e3de2dd4b73a9d6b7d4823b8598
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06956050B2

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