Acetic Acid → HCID 22561914, 화합물

HRID 983029노트

반응식

HRID 983029 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([OH:22])C.C(O)(=O)C.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CC(O)(C)C.[Zn].O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][C:14](=[O:22])[NH:15]3)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

참가 물질

8

반응물 4

HCID 176Acetic Acid2회HCID 702EthanolHCID 21124087PyridiniumtribromideHCID 225616844-(3,4-dimethoxy-phenyl)1H-indole

생성물 1

HCID 22561914HCID 22561914, 화합물수율 65%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 962Water용매HCID 6386tert-Butanol용매

실험 절차

To the suspension of 4-(3,4-dimethoxy-phenyl)-1H-indole (14.7 g, 58 mmol) in t-BuOH: ethanol: acetic acid (367 mL: 217 mL: 113 mL) was added pyridinium tribromide (55.68 g, 174 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added more acetic acid (287 mL). Zinc dust (18.95 g, 290 mmol) was added to the reaction mixture portionwise. After stirring for one hour, water was added to the reaction. The unreacted zinc was filtered off and most of the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate, washed with water (6×), sat. NaHCO3 (2×), brine (3×), dried over Na2SO4, concentrated and triturated with ether to give 10.14 g (65%) of 4-(3,4-dimethoxy-phenyl)-1,3-dihydro-indol-2-one as an earth colored solid.

후처리

  1. stirringAfter stirring for one hour
  2. filtrationThe unreacted zinc was filtered off and most of the solvent
  3. customwas removed under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water (6×), sat. NaHCO3 (2×), brine (3×)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customtriturated with ether

출처 및 근거

ORD 기록
ord-92d31f892f444d61b8be89c4eb00fc2e
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06861418B2

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