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1-[5-(2-Naphthyl)-1H-imidazol-2-yl]nonane-1,8-dione → 6-(2-ethyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)hexan-1-one

HRID 913058
ノート
印刷プレビュー

反応式

HRID 913058 の反応式
C1C2C(=CC=CC=2)C=CC=1C1NC(C(=O)CCCCCCC(=O)C)=NC=1.[CH:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][C:28]=1[C:37]1[N:38]=[CH:39][N:40]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[CH:41]=1.[Li]CCCC.[CH2:55]([C:57]1([CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][C:67](N(OC)C)=[O:68])[O:61][CH2:60][CH2:59][O:58]1)[CH3:56]>C1COCC1.CCCCCC.O>[CH2:55]([C:57]1([CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][C:67]([C:39]2[N:40]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[CH:41]=[C:37]([C:28]3[CH:29]=[CH:30][C:31]4[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:27]=3)[N:38]=2)=[O:68])[O:58][CH2:59][CH2:60][O:61]1)[CH3:56]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 673820661-[5-(2-Naphthyl)-1H-imidazol-2-yl]nonane-1,8-dioneHCID 673822734-(2-Naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazoleHCID 867614186-(2-ethyl-1,3-dioxolan-2-yl)-N-methoxy-N-methylhexanamideHCID 178418339Butyllithium

生成物 1

HCID 673819946-(2-ethyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)hexan-1-one

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

To a solution of Example 5, 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 6-(2-ethyl-1,3-dioxolan-2-yl)-N-methoxy-N-methylhexanamide (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 product was used without purification in the next step. MS (ES) C30H42N2O4Si requires: 523, found: 524 (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 product was used without purification in the next step

出典と根拠

ORDレコード
ord-fdb4b953be124267ae5cbe99ee929abf
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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