Dichloromethane → 5-Benzyl-3H-isobenzofuran-1-one

HRID 706174

反応式

HRID 706174 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[O:6][CH2:5]2.[Br-].[CH2:13]([Zn+])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[CH2:13]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[O:6][CH2:5]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 6031445-BromophthalideHCID 178419772HCID 178419772、化合物

生成物 1

HCID 584166365-Benzyl-3H-isobenzofuran-1-one収率 43.6%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 5-bromo-3H-isobenzofuran-1-one (14 mmol, 3.04 g), benzylzinc bromide solution (0.5 M in THF, 28 mmol, 56 mL), [1,1′bis(diphenylphosphino)-ferrocene]dichloropalladium(II) 1:1 complex with CH2Cl2 (0.07 mmol, 57 mg), and anhydrous 1.4-dioxane (70 mL) was refluxed with stirring under nitrogen for 40 h. After cooling to ambient temperature silica gel was added and the mixture was concentrated in vacuo. The residue was added on top of a chromatography column filled with silica gel. Elution with hexanes:ethyl acetate=9:1 gave a yellow solid. Further purification by recrystallization from ethyl acetate/hexanes gave the title compound (1.37 g) as white needles; 1H NMR (CDCl3, 200 MHz): δ=7.83 (d, 1H), 7.16 to 7.39 (m, 7H), 5.26 (s, 2H), 4.11 (s, 2H).

後処理

  1. temperaturewas refluxed
  2. additionwas added
  3. concentrationthe mixture was concentrated in vacuo
  4. additionThe residue was added on top of a chromatography column
  5. additionfilled with silica gel
  6. washElution with hexanes
  7. customethyl acetate=9:1 gave a yellow solid
  8. customFurther purification
  9. customby recrystallization from ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-45552c40f96d4f20b95aa36c9fb6802e
出典データセット
uspto-grants-2015_11
特許番号
US09174976B2

関連ノート

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