Sodium hydride → 4-(4-Phenylbutoxy)-1,2-dinitrobenzene

HRID 412696

反応式

HRID 412696 の反応式
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[N+:14]([C:17]1[CH:18]=[C:19](Cl)[CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24])([O-:16])=[O:15]>C1COCC1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:19]2[CH:20]=[CH:21][C:22]([N+:23]([O-:25])=[O:24])=[C:17]([N+:14]([O-:16])=[O:15])[CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 330974-Chloro-1,2-dinitrobenzeneHCID 76889Benzenebutanol

生成物 1

HCID 185379134-(4-Phenylbutoxy)-1,2-dinitrobenzene収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-Phenyl-1-butanol (1 mL, 6.49 mmol) in THF (3 mL) was combined under dry nitrogen with sodium hydride (0.26 g, 6.5 mmol) in a 60% mineral oil dispersion. The mixture was stirred vigorously for 5 minutes, combined with 3,4-dinitrochlorobenzene (1.3 g, 6.42 mmol) and then stirred 10 hours at room temperature. The mixture was partitioned between diethyl ether and 3N hydrochloric acid. The aqeuous layer was separated and extracted several times with diethyl ether. The combined organic layers were dried (MgSO4), filtered and concentrated by rotary evaporation. The residue was purfied by flash chromatography (9:1 hexanes/diethyl ether) to provide 4-(4-phenylbutoxy)-1,2-dinitrobenzene (1.16 g, 72% yield); 1H-NMR (300 Mhz, CDCL3): 7.84 (d, 1H, J=10.0 Hz), 7.19-7.36 (m, 5H), 7.00-7.06 (m, 2H), 4.10 (t, 2H, J=5.7 Hz), 2.73 (t, 2H, J=6.5 Hz), 1.89 (m, 4H).

後処理

  1. stirringstirred 10 hours at room temperature
  2. customThe mixture was partitioned between diethyl ether and 3N hydrochloric acid
  3. customThe aqeuous layer was separated
  4. extractionextracted several times with diethyl ether
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-18edf7757a4747c7a02c3776e4fa8613
出典データセット
uspto-grants-2003_05
特許番号
US06562854B2

関連ノート

読み込み中…