Dichloromethane → 7-(furan-3-yl)-3,4-dihydro-2H-1-benzopyran-4-one

HRID 63621

反応式

HRID 63621 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]C2.[O:13]1[CH:17]=[CH:16][C:15](B2OC(C)(C)C(C)(C)O2)=[CH:14]1.C(Cl)Cl.C([O-])(O)=[O:31].[Na+]>O1CCOCC1.CCOC(C)=O.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]>[O:13]1[CH:17]=[CH:16][C:15]([C:2]2[CH:11]=[CH:10][C:9]3[C:8](=[O:12])[CH2:7][CH2:6][O:31][C:4]=3[CH:3]=2)=[CH:14]1

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 27739962-(Furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 101050696-Bromo-1-tetralone

生成物 1

HCID 1185979197-(furan-3-yl)-3,4-dihydro-2H-1-benzopyran-4-one収率 83%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-one (1.5 g, 6.6 mmol) in dioxane (6 mL) was added 2-(furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.92 g, 9.9 mmol), Pd(dppf)Cl2.DCM (540 mg, 0.66 mmol) and sat. NaHCO3 (2 mL). The mixture was stirred at 100° C. for 4 h under nitrogen. The mixture was cooled to rt and diluted with EtOAc, filtered, and concentrated. The residue was purified by silica gel chromatography (4:1 PE:EtOAc) to give 1.18 g (83%) of the title compound as white solid. 1H NMR (400 MHz, CDCl3): δ 2.82 (2H, t, J=6.2 Hz), 4.56 (2H, t, J=6.4 Hz), 6.71 (1H, s), 7.07 (1H, s), 7.14 (1H, d, J=8.4 Hz), 7.50 (1H, s), 7.81 (1H, s), 7.88 (1H, d, J=8.4 Hz). [M+H] Calc'd for C13H10O3, 215. Found, 215.

後処理

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (4:1 PE:EtOAc)

出典と根拠

ORDレコード
ord-75d1b073b3e7499f9287b84fd8750187
出典データセット
uspto-grants-2016_09
特許番号
US09447046B2

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