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Water → 7-(2-Methyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)heptan-1-one

HRID 913056
ノート
印刷プレビュー

反応式

HRID 913056 の反応式
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[N:12]=[CH:13][N:14]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=1.[Li]CCCC.CON(C)[C:32](=[O:45])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]1([CH3:44])[O:43][CH2:42][CH2:41][O:40]1.O>C1COCC1.CCCCCC>[CH3:44][C:39]1([CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][C:32]([C:13]2[N:14]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=[C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[N:12]=2)=[O:45])[O:40][CH2:41][CH2:42][O:43]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 673822734-(2-Naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazoleHCID 86645337N-methoxy-N-methyl-7-(2-methyl-1,3-dioxolan-2-yl)heptanamideHCID 178418339Butyllithium

生成物 1

HCID 673819037-(2-Methyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)heptan-1-one

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回
HCID 8058Hexane溶媒

実験手順

To a solution of E2 (1.0 eq.) in THF (0.1 M solution) at −78° C. was added a solution of n-BuLi (1.3 eq.) in hexane. The solution was stirred for 30 min and then a solution of N-methoxy-N-methyl-7-(2-methyl-1,3-dioxolan-2-yl)heptanamide (1.5 eq.) in THF was slowly added. The reaction mixture was stirred for 1 hr at −78° C. and then 1 hr at RT. Then water was added and the aqueous phase was extracted with EtOAc. The combined organic extracts were dried (MgSO4) and the solvent was removed under reduced pressure. The crude was purified by column chromatography on silica gel eluting with 20-50% EtOAc/petroleum ether to obtain E3 as yellow solid. 1H NMR (300 MHz, CDCl3) δ: 8.32 (1H, s), 7.96-7.81 (4H, m), 7.68 (1H, s) 7.53-7.42 (2H, m), 5.85 (2H, s), 3.92 (4H, s), 3.64 (2H, t, J=8.2 Hz), 3.26 (2H, t, J=8.2 Hz), 1.77 (2H, m), 1.69-1.36 (8H, m), 1.31 (3H, s), 0.97 (2H, t, J=8.2 Hz), 0.19 (9H, s). MS (ES) C30H42N2O4Si requires: 522, found: 523 (M+H)+.

後処理

  1. stirringThe reaction mixture was stirred for 1 hr at −78° C.
  2. custom1 hr
  3. customat RT
  4. extractionthe aqueous phase was extracted with EtOAc
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customthe solvent was removed under reduced pressure
  7. customThe crude was purified by column chromatography on silica gel eluting with 20-50% EtOAc/petroleum ether

出典と根拠

ORDレコード
ord-57181833e29c4f529f880cba0a321863
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08026265B2

反応ノート

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