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

HRID 412696

반응식

HRID 412696 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-18edf7757a4747c7a02c3776e4fa8613
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562854B2

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