Hydrogen Peroxide → 2-[6-Fluoro-2-methyl-3-[(4-methylsulfonylphenyl)methylidene]inden-1-yl]acetic acid

HRID 567191

반응식

HRID 567191 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

8

반응물 5

HCID 784Hydrogen PeroxideHCID 53525-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acidHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 1148662-[6-Fluoro-2-methyl-3-[(4-methylsulfonylphenyl)methylidene]inden-1-yl]acetic acid수율 89%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

5-Fluoro-2-methyl-1-(p-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-(p-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%. (R1=5-fluoro; R2=CH3; R3=hydrogen; R4=COOH; R5=CH3SO2; n=1).

후처리

  1. temperaturecooled
  2. customto react for 18 hours at −10° C
  3. filtrationExcess sodium bicarbonate is filtered off
  4. filtrationThe resulting product is then filtered
  5. washwashed with methanol
  6. customA tetrahydrofuran/diisopropyl ether combination can be used for product recrystallization
  7. customReaction yield is 89%

출처 및 근거

ORD 기록
ord-3ff3e26b871e431db6ba2e01081c45b9
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06177471B1

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