Methyl iodide → 4,6-Difluoro-2-methyl-2,3-dihydro-1H-inden-1-one

HRID 574637노트

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HRID 574637 반응식
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12].[CH:13]([N-]C(C)C)(C)C.[Li+].IC.C([O-])(O)=O.[Na+]>O1CCCC1>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:13])[C:6]2=[O:12]

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamideHCID 109539204,6-difluoro-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 224570084,6-Difluoro-2-methyl-2,3-dihydro-1H-inden-1-one수율 21.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

According to Scheme 3, step 1: to a solution of 4,6-difluoro-indan-1-one (5.0 g, 29.8 mmol) in dry tetrahydrofuran (100 ml) at −78° C. a 2M solution of lithiumdiisopropylamide (16.4 ml, 32.7 mmol) in tetrahydrofuran was added dropwise and the mixture was stirred for 1 h at −78° C. Then iodomethane (4.64 g, 32.7 mmol) was added and the mixture was slowly warmed to 25° C. After addition of aqueous saturated NaHCO3 the mixture was extracted 3 times with ethyl acetate. The combined organic layers were dried over Na2SO4 and filtered, solvents were evaporated in vacuo. The crude product was purified by silica gel chromatography (eluting with 0% to 100% ethyl acetate in heptane to give 1.15 g of 4,6-Difluoro-2-methyl-indan-1-one (7a).

후처리

  1. temperaturethe mixture was slowly warmed to 25° C
  2. extractionwas extracted 3 times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customsolvents were evaporated in vacuo
  6. customThe crude product was purified by silica gel chromatography (
  7. washeluting with 0% to 100% ethyl acetate in heptane

출처 및 근거

ORD 기록
ord-d63504172c914fc7abc694400a02d4d2
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034897B2

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