Iodoethane → HCID 69693476、化合物

HRID 967814ノート

反応式

HRID 967814 の反応式
[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]

参加物

7

反応物 4

HCID 6340IodoethaneHCID 8058HexaneHCID 69693088HCID 69693088、化合物HCID 178418339Butyllithium

生成物 1

HCID 69693476HCID 69693476、化合物収率 92%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-30c91e3de2dd4b73a9d6b7d4823b8598
出典データセット
uspto-grants-2005_10
特許番号
US06956050B2

反応ノート

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