Water → 1H-Indole, 4-methoxy-1-(phenylmethyl)-

HRID 51462

반응식

HRID 51462 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C=O)C>[CH2:14]([N:9]1[C:10]2[C:6](=[C:5]([O:4][CH3:3])[CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1383634-Methoxy-1H-indole

생성물 1

HCID 107285831H-Indole, 4-methoxy-1-(phenylmethyl)-

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

NaH (7.7 g, 191.7 mmol) was added portionwise to a 0° C. solution of 4-methoxyindole (21.7 g, 147 mmol) in 750 mL of anhydrous DMF. After 15 min, the slurry was treated with benzyl bromide (17.5 mL, 147 mmol). The reaction mixture was allowed to warm to ambient temperature and stir overnight. The reaction mixture was poured into 1 L of H2O. The layers were separated, and the aqueous phase was extracted with EtOAc (2×200 mL). The combined organic layers were washed with H2O (4×500 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2; hexanes) to give 32.9 g (138.6 mmol; 94%) of the title compound as a white solid. Electrospray MS 238 (M+1);

후처리

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with EtOAc (2×200 mL)
  3. washThe combined organic layers were washed with H2O (4×500 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography (SiO2; hexanes)

출처 및 근거

ORD 기록
ord-97edd9a9e9384aa68947fff24ad4d889
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713645B1

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