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

HRID 659107

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

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)

Workup

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

Sources & evidence

ORD record: ord-d2632edca8e64415a05b896613de4e3f
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080567B2

Linked notes

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