HCID 11197766、化合物 → HCID 67354173、化合物

HRID 1846150ノート

反応式

HRID 1846150 の反応式
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:10]([CH3:23])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Li]C1C=CC=CC=1.Br[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C1COCC1.CCCCCC>[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:10]([CH2:23][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][O:41][CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

参加物

6

反応物 3

HCID 11197766HCID 11197766、化合物HCID 67355477HCID 67355477、化合物HCID 178506676HCID 178506676、化合物

生成物 1

HCID 67354173HCID 67354173、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

To a stirred solution at −78° C. containing 1.42 g (4.63 mmol) of 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-benzyloxy-4,6-dimethylpyridine (16) in 20 mL of anhydrous THF were added 5.15 mL (9.27 mmol) of a 1.8 M solution of PhLi in hexane followed by 1.45 g (4.63 mmol) of 9-bromo-1-(benzyloxy)nonane (1). The reaction mixture was stirred under argon atmosphere at −78° C. for 30 min. then the reaction mixture was warmed to room temperature slowly, and the reaction mixture was stirred 30 min. The reaction was quenched with saturated aqueous NaHCO3 and the poured into 150 mL of water. The mixture was then extracted with two portions of 150 mL of ethyl acetate. The combined organic solution was then washed with a portion of 100 mL of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with hexanes-ethyl acetate 4:1 gave the expected product as light yellow oil: yield 1.22 g (49%) 1H-NMR (CDCl3) δ 7.54-7.37 (m, 10H), 6.93, (s, 1H), 5.94 (s, 2H), 4.95 (s, 2H), 4.55 (s, 2H), 3.52 (t, 2H, J=6.4), 2.91 (t, 2H, J=8.0) 2.39 (s, 3H), 2.51 (s, 6H), 1.82 (m, 2H), 1.65 (m, 2H), 1.33 (m, 12H); 13C-NMR (CDCl3) δ 155.94, 150.86, 146.89, 142.59, 138.80, 136.92, 128.69, 128.49, 128.38, 127.81, 127.65, 127.49, 121.75, 106.55, 75.30, 72.89, 70.55, 32.21, 29.85, 29.68, 29.63, 29.60, 29.59, 29.57, 29.53, 28.99, 26.27, 16.42, 13.30.

後処理

  1. temperaturethe reaction mixture was warmed to room temperature slowly
  2. stirringthe reaction mixture was stirred 30 min
  3. customThe reaction was quenched with saturated aqueous NaHCO3
  4. additionthe poured into 150 mL of water
  5. extractionThe mixture was then extracted with two portions of 150 mL of ethyl acetate
  6. washThe combined organic solution was then washed with a portion of 100 mL of brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under diminished pressure
  9. customThe residue was purified by chromatography on a silica gel column
  10. washElution with hexanes-ethyl acetate 4:1

出典と根拠

ORDレコード
ord-05fda82611704499800ec6848538a95c
出典データセット
uspto-grants-2015_02
特許番号
US08952025B2

反応ノート

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