Diethyl (ethoxymethylene)malonate → HCID 86738854, compound

HRID 850913Notes

Reaction equation

[NH2:1][C:2]1[CH:8]=[CH:7][C:6](=[O:9])[C:5]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(O[CH:21]=[C:22]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24])C>ClCCl.CC(C)=O>[CH2:26]([O:25][C:23](=[O:24])[C:22](=[CH:21][NH:1][C:2]1[CH:8]=[CH:7][C:6](=[O:9])[C:5]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][CH:3]=1)[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:27]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 5-amino-2-benzyloxy-2,4,6-cycloheptatrien-1-one (10 g), described in example 1b, and diethyl ethoxymethylenemalonate (100 ml) was heated at 140° C. for 1.5 hr. The cooled reaction mixture was subjected to chromatography on silica gel using dichloromethane-acetone (9:1) as the eluant. The pure fractions were pooled to give 2-[(4-benzyloxy-5-oxo-1,3,6-cycloheptatrien-1-yl)aminomethylene]propanedioic acid diethyl ester (V; R7 =OCH2C6H5 and R8 =C2H5); nmr (CDCl3) δ1.3 (m 6H), 4.2 (m, 4H), 5.2 (s, 2H), 7.2 (m, 2H), 7.2 (m, 9H), 8.25 (d, 1H), 10.9 (d, 1H); ir (CHCl3) 3490, 3240, 1700, 1690, 1570; uv λmax (MeOH) 279 nm (ε10,410), 224 (27,380).

Workup

customThe cooled reaction mixture

Sources & evidence

ORD record: ord-b0973bcdf36e49b79b0253a81016e5ab
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04382088

Reaction notes

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