반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]2[C:8](=O)[CH2:9][O:10][C:11]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:12]=3[C:13]=2[N:14]=1)=[O:4].[Br-].[CH3:22][O:23][C:24]([CH2:26][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:25].[H-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]2/[C:8](=[CH:26]/[C:24]([O:23][CH3:22])=[O:25])/[CH2:9][O:10][C:11]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:12]=3[C:13]=2[N:14]=1)=[O:4]참가 물질
반응물 3
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- 70 °C
실험 절차
To a stirred solution of 9-Bromo-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (100 mg, 0.28 mmol) in THF (7 mL), was added Methoxycarbonylmethyl(triphenyl)phosphonium Bromide (120 mg, 0.28 mmol), NaH (6.8 mg, 0.28 mmol). The reaction mixture was heated to 70° C. overnight. The mixture was cooled to room temperature and partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated in vacuo, and purified by flash column chromatography to afford 9-Bromo-4-[1-methoxycarbonyl-meth-(E)-ylidene]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (50 mg, 43%) as a light yellow solid. LC-MS (ESI & APCI): 412.3 (M+2).
후처리
- temperatureThe mixture was cooled to room temperature
- custompartitioned between EtOAc and H2O
- extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- custompurified by flash column chromatography
출처 및 근거
- ORD 기록
- ord-4db7007d1ca04f7bbf40987094391164
- 출처 데이터셋
- uspto-grants-2015_05
- 특허 번호
- US09034866B2
연결된 노트
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