Diisobutylaluminum hydride → HCID 86614859, 화합물

HRID 229626노트

반응식

HRID 229626 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:5](N(OC)C)=[O:6].[CH3:17][CH:18](C[AlH]CC(C)C)C>C1COCC1.Cl.CCOC(C)=O>[CH2:17]([C:3]1[C:2]([F:1])=[C:13]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:11][C:4]=1[CH:5]=[O:6])[CH3:18]

참가 물질

6

반응물 2

HCID 14487Diisobutylaluminum hydrideHCID 577580833-Fluoro-N-methoxy-N-methyl-4-nitrobenzamide

생성물 1

HCID 86614859HCID 86614859, 화합물수율 88%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of THF (800 mL) cooled in an ice-salt/water bath was added 3-fluoro-N-methoxy-N-methyl-4-nitrobenzamide followed by addition of 1 M DIBAL in THF by addition funnel over 30 min. The solution was allowed to stir under N2 for 1 h. The reaction mixture was then carefully diluted with 1N HCl (500 mL) and EtOAc (500 mL), transferred to separatory funnel, and separated. The organic phase was washed with 1N HCl (3×250 mL), 1N NaOH (2×250 mL), and water (250 mL). All aqueous layers were back extracted with EtOAc (2×250 mL). The organic layers were combined, dried (MgSO4), filtered, and concentrated in vacuo to afford 67 g of the above compound (396 mmol, yield 88%). 1H-NMR (DMSO-d6) δ 10.06 (s, 1H), 8.36 to 8.32 (t, J=7.8 Hz, 1H), 8.06 to 8.03(d, J=11.2 Hz, 1H), 7.95 to 7.93 (d, J=9.1 Hz, 1H).

후처리

  1. customtransferred to separatory funnel
  2. customseparated
  3. washThe organic phase was washed with 1N HCl (3×250 mL), 1N NaOH (2×250 mL), and water (250 mL)
  4. extractionAll aqueous layers were back extracted with EtOAc (2×250 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-76e09850a7bc4cf7ad61d0caa1859361
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563791B2

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