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

HRID 659107

반응식

HRID 659107 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매2회

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온도
90 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-d2632edca8e64415a05b896613de4e3f
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080567B2

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