Water → HCID 67355477、化合物

HRID 1846149ノート

反応式

HRID 1846149 の反応式
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[C:12]([CH3:14])[C:11]([OH:15])=[C:10]([CH3:16])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[H-].[Na+].O>C1COCC1>[CH3:7][C:4]1[N:3]([C:8]2[CH:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:10]([CH3:16])[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 67353847HCID 67353847、化合物

生成物 1

HCID 67355477HCID 67355477、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution containing 1.18 g (5.50 mmol) of 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-hydroxy-4,6-dimethylpyridine (15) in 20 mL of anhydrous THF were added 1.20 mL (10.10 mmol) of benzyl bromide followed by 440 mg (11.00 mmol) of 60% sodium hydride suspension in mineral oil. The reaction mixture was stirred at room temperature under argon atmosphere overnight. The reaction mixture was poured into 150 mL of water and extracted with two portions of 100 mL of ethyl acetate. The combined organic solution was 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 1.42 g (84%). 1H-NMR (CDCl3) δ 6.98 (s, 1H), 5.91 (s, 2H), 4.94 (s, 2H), 2.58 (s, 3H), 2.37 (s, 3H), 2.17 (s, 6H); 13C-NMR (CDCl3) δ 152.02, 151.03, 146.64, 141.95, 136.73, 128.60, 128.33, 127.89, 121.94, 106.44, 74.59, 19.48, 16.18, 13.08.

後処理

  1. extractionextracted with two portions of 100 mL of ethyl acetate
  2. washThe combined organic solution was washed with a portion of 100 mL of brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under diminished pressure
  5. customThe residue was purified by chromatography on a silica gel column
  6. washElution with hexanes-ethyl acetate 4:1

出典と根拠

ORDレコード
ord-06d7db4646d94bb093c70aefafbd5323
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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