1,2-Dimethoxyethane → 1-(2'-(Benzyloxy)-3'-tert-butylbiphenyl-3-yl)ethanone

HRID 45473ノート

反応式

HRID 45473 の反応式
[CH2:1]([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1B1OC(C)(C)C(C)(C)O1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)(=[O:30])[CH3:29].C(COC)OC.C(=O)(O)[O-].[Na+]>O.[Pd].C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:14]([C:15]([CH3:16])([CH3:17])[CH3:18])=[CH:13][CH:12]=[CH:11][C:10]=1[C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([C:28](=[O:30])[CH3:29])[CH:36]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

9

反応物 4

HCID 80711,2-DimethoxyethaneHCID 516892Sodium BicarbonateHCID 27343103-Acetylphenylboronic acidHCID 58238577(2-(Benzyloxy)-3-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 582385981-(2'-(Benzyloxy)-3'-tert-butylbiphenyl-3-yl)ethanone収率 87%

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of crude 35 (3.88 g, 10 mmol), 3-acetylphenyl boronic acid (1.8 g, 11 mmol, 1.1 equiv.), bis(triphenylphosphine)palladium(II) dichloride (20 mg), glyme (5.5 mL) and sodium bicarbonate (2.7 g) in water (55 mL) was kept at reflux under nitrogen for 2 hr. Additional palladium catalyst (20 mg) was added and reflux continued for 3 hr. After cooling the reaction mixture was diluted with ethyl acetate (150 mL) and washed with saturated sodium bicarbonate (100 mL) and water (2×100 mL). The organic extract was dried over sodium sulfate and filtered. The solvent was removed in a rotary evaporator and the crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in heptane (4 L) to afford 36 (3.12 g, 87%).

後処理

  1. temperatureat reflux under nitrogen for 2 hr
  2. temperaturereflux
  3. temperatureAfter cooling the reaction mixture
  4. washwashed with saturated sodium bicarbonate (100 mL) and water (2×100 mL)
  5. extractionThe organic extract
  6. dry with materialwas dried over sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed in a rotary evaporator
  9. customthe crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in heptane (4 L)

出典と根拠

ORDレコード
ord-57a0a49e15e24339920b1e9008819350
出典データセット
uspto-grants-2013_09
特許番号
US08541522B2

反応ノート

読み込み中…