Undec-4-ene → 4-(azidomethyl)-1H-indole
반응식
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH2:10]O)[C:4]=2[CH:3]=[CH:2]1.C1(P([N:26]=[N+:27]=[N-:28])(C2C=CC=CC=2)=O)C=CC=CC=1.CCCCCCC=CCCC>O1CCCC1>[N:26]([CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2)=[N+:27]=[N-:28]참가 물질
5
실험 절차
To a solution of 1H-indole-4-methanol (71 mg, 0.48 mmol) in tetrahydrofuran (1 mL) at 0° C. was added diphenylphosphoryl azide (156 μL, 0.72 mmol) followed by 1,8-diaza[5.4.0]undec-7-ene (87.4 μL, 0.58 mmol). The cooling bath was removed and the solution was allowed to stir for 5 h. The solvent was evaporated and ethyl acetate was added. The solution was washed with 1 M HCl and brine, dried (MgSO4), filtered, concentrated and chromatographed (12% ethyl acetate/hexanes) to give 4-(azidomethyl)-1H-indole (1.496 g, 88%) as an oil.
후처리
- customThe cooling bath was removed
- customThe solvent was evaporated
- additionethyl acetate was added
- washThe solution was washed with 1 M HCl and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customchromatographed (12% ethyl acetate/hexanes)
출처 및 근거
- ORD 기록
- ord-655cc2b235f04d2eb70d4b678afdbf13
- 출처 데이터셋
- uspto-grants-2004_10
- 특허 번호
- US06803384B2
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