Methyl Acrylate → 3-{3-[2-Oxo-2-(5-phenyl-furan-2-yl)-ethyl]-phenyl}-acrylic acid methyl ester

HRID 659107

反応式

HRID 659107 の反応式
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25].C(N(CC)CC)C.Br[C:37]1[CH:38]=[C:39]([CH2:43][C:44]([C:46]2[O:47][C:48]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[CH:49][CH:50]=2)=[O:45])[CH:40]=[CH:41][CH:42]=1>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:28][O:27][C:23](=[O:26])[CH:24]=[CH:25][C:41]1[CH:42]=[CH:37][CH:38]=[C:39]([CH2:43][C:44](=[O:45])[C:46]2[O:47][C:48]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[CH:49][CH:50]=2)[CH:40]=1

参加物

7

反応物 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 596547282-(3-Bromo-phenyl)-1-(5-phenyl-furan-2-yl)-ethanone

生成物 1

HCID 684146713-{3-[2-Oxo-2-(5-phenyl-furan-2-yl)-ethyl]-phenyl}-acrylic acid methyl ester

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒2 回

反応条件

温度
90 °C

実験手順

Tri(o-toly)phosphine (25 mg, 0.082 mmol) and palladium(II) acetate (9 mg, 0.041 mmol) in acetonitrile (1 mL) was added to a mixture of methyl acrylate (84 mg, 0.98 mmol) and triethylamine (329 mg, 3.26 mmol). Aryl bromide (25) (278 mg, 0.82 mmol) in acetonitrile (3 mL) was then added and the reaction mixture heated in a CEM Discover microwave for 45 minutes at 90° C. The solvent was concentrated in vacuo, and the crude product was purified by Flash Master Jones Chromatography using a 25 g silica cartridge eluting with 5-17% EtOAc in heptane. Yield: 222 mg, 78%; LC-MS tr 1.62 min; HPLC Purity: 100%; MS (ES+) m/z 347 (M+H)

後処理

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe crude product was purified by Flash Master Jones Chromatography
  3. washeluting with 5-17% EtOAc in heptane

出典と根拠

ORDレコード
ord-d2632edca8e64415a05b896613de4e3f
出典データセット
uspto-grants-2011_12
特許番号
US08080567B2

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