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

HRID 45469ノート

反応式

HRID 45469 の反応式
FC(F)(F)S(O[C:7]1[C:8]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)(=O)=O.[C:29]([C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)(=[O:31])[CH3:30].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>[CH2:20]([O:19][C:8]1[C:9]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][CH:11]=[CH:12][C:7]=1[C:36]1[CH:35]=[CH:34][CH:33]=[C:32]([C:29](=[O:31])[CH3:30])[CH:37]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参加物

9

反応物 4

HCID 80711,2-DimethoxyethaneHCID 516892Sodium BicarbonateHCID 27343103-Acetylphenylboronic acidHCID 582385672-(Benzyloxy)biphenyl-3-yl trifluoromethanesulfonate

生成物 1

HCID 582385951-(2'-(Benzyloxy)-3'-phenylbiphenyl-3-yl)ethanone収率 100%

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 31 (3.18 g, 7.8 mmol), 3-acetylphenylboronic acid (1.6 g, 9.76 mmol, 1.25 equiv.), glyme (5 mL), bis(triphenylphosphine)palladium(II) dichloride (25 mg) and sodium bicarbonate (2.1 g) in water (40 mL) was kept at reflux under nitrogen for 11 hr with additional palladium catalyst (2×30 mg) added after 3 and 7 hr. After cooling, the reaction mixture was diluted with ethyl acetate (200 mL) and washed with water (2×800 mL). The organic layer 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 (120 g) with 2% ethyl acetate in heptane (4 L) to afford 32 (2.9 g, 100%).

後処理

  1. additionadded after 3 and 7 hr
  2. temperatureAfter cooling
  3. washwashed with water (2×800 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed in a rotary evaporator
  7. customthe crude product was purified by chromatography on silica (120 g) with 2% ethyl acetate in heptane (4 L)

出典と根拠

ORDレコード
ord-0f16a94773714b63b0a4c8cdcdc0b2f2
出典データセット
uspto-grants-2013_09
特許番号
US08541522B2

反応ノート

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