Ethyl Acetate → Ethyl 1-(6-phenylpyridin-3-yl)cyclopropanecarboxylate

HRID 557819ノート

反応式

HRID 557819 の反応式
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[N:13]=[CH:12][C:11]([C:14]2([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OCC)(=O)C>O.C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:22]1([C:8]2[N:13]=[CH:12][C:11]([C:14]3([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

9

反応物 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86602273Ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate

生成物 1

HCID 66661635Ethyl 1-(6-phenylpyridin-3-yl)cyclopropanecarboxylate

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

Sodium carbonate (42.4 mg, 0.400 mmol) in water (0.20 mL) was added to a mixture of ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate (45.1 mg, 0.200 mmol), Phenylboronic acid (24.4 mg, 0.200 mmol) and tetrakis(triphenylphosphine)palladium(0) (7.15 mg) in toluene (200.0 μL) and ethanol (100.0 μL). The resulting mixture was irradiated by microwave at 120° C. for 15 minutes. Ethyl acetate (5 mL) was then added to the mixture. The resulting mixture was washed with water followed by brine. The organic layer was dried over Na2SO4, then filtered, and then concentrated under reduced pressure. The residue was purified by flash chromatography with ethyl acetate/hexane to give ethyl 1-(6-phenylpyridin-3-yl)cyclopropanecarboxylate.

後処理

  1. customThe resulting mixture was irradiated by microwave at 120° C. for 15 minutes
  2. washThe resulting mixture was washed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-32961ba308614a839d8e3bb0a38a77c9
出典データセット
uspto-grants-2011_11
特許番号
US08058288B2

反応ノート

読み込み中…