반응식
C[O-].[Na+].[F:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:23])=[O:22])=[CH:17][CH:16]=1)[C:9]([CH3:24])=[C:8]2[CH2:25][C:26]([OH:28])=[O:27].C(=O)(O)[O-:30].[Na+].OO.[H][H]>CO.C(#N)C>[F:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:23])(=[O:30])=[O:22])=[CH:17][CH:16]=1)[C:9]([CH3:24])=[C:8]2[CH2:25][C:26]([OH:28])=[O:27]참가 물질
반응물 5
생성물 1
시약·촉매·용매 2
반응 조건
- 온도
- 0 °C
실험 절차
5-fluoro-2-methyl-1-(ρ-methylsulfonylbenzylidene)-3-indenyl acetic acid is prepared by adding sodium methoxide (4.4M in MeOH, 68.5 ml, 0.3 mol) dropwise to a stirred cooled mixture of 5-fluoro-2-methyl-1-(ρ-methylsulfinylbenzylidene)-3-indenyl acetic acid (100 g, 0.281 mol) in methanol (250 ml) and acetonitrile (500 ml). Sodium bicarbonate (0.56 mol) and hydrogen peroxide (30% in water, 0.56 mol) are added and allowed to react for 18 hours at -10° C. Excess sodium bicarbonate is filtered off, and cooled filtrate (0° C.) neutralized dropwise to pH 7 with 1M hydrochloric acid (350 ml). The resulting product is then filtered and washed with methanol. A thin layer chromatography system to check for purity utilizes chloroform:methyl isobutyl ketone (8:2); the Rf value is 0.21. A tetrahydrofuran/diisopropyl ether combination can be used for product recrystallization. Reaction yield is 89%. The product has a mp of 205°-206° C. (R1 =hydrogen; R2 =CH3 ; R3 =5-fluoro; R4 =hydrogen; R5 =CH3SO2 --)
후처리
- temperaturecooled
- customto react for 18 hours at -10° C
- filtrationExcess sodium bicarbonate is filtered off
- filtrationThe resulting product is then filtered
- washwashed with methanol
- customA tetrahydrofuran/diisopropyl ether combination can be used for product recrystallization
- customReaction yield is 89%
출처 및 근거
- ORD 기록
- ord-c16e649d53464025befd22f716f121e9
- 출처 데이터셋
- uspto-grants-1997_07
- 특허 번호
- US05643959
연결된 노트
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