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

HRID 574637ノート

反応式

HRID 574637 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d63504172c914fc7abc694400a02d4d2
出典データセット
uspto-grants-2015_05
特許番号
US09034897B2

反応ノート

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