[2-(Ethoxycarbonyl)-1-benzothien-6-yl](methyl)malonic acid → 2-[2-(Ethoxycarbonyl)-1-benzothien-6-yl]propanoic acid

HRID 500666Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[CH:14]=[C:13]([C:15](C)([C:19](O)=O)[C:16]([OH:18])=[O:17])[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2]>O>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[CH:14]=[C:13]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 210 °C

Procedure

[2-(ethoxycarbonyl)-1-benzothien-6-yl](methyl)malonic acid (0.19 g, 0.590 mmol) was suspended in H2O (5 mL) before heating at 210° C. in a microwave reactor for 40 seconds. The suspension was diluted with H2O (50 mL) and the products extracted into EtOAc (2×75 mL). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo to give 0.15 g of product (white solid, 91%). 1H NMR (DMSO-d6) δ 12.41 (br s, 1H), 8.14 (s, 1H), 7.95 (br s, 1H), 7.94 (d, J=8.4 Hz, 1H), 7.37 (dd, J=8.4, 1.8 Hz, 1H), 4.32 (q, J=7.2 Hz, 2H), 3.81 (q, J=7.2 Hz, 1H), 1.40 (d, J=7.2 Hz, 3H), 1.31 (t, J=7.2 Hz, 3H).

Workup

extractionthe products extracted into EtOAc (2×75 mL)
washThe combined organic extracts were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e6454dd3fa7d478d8860e9a19e44deac
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772238B2

Reaction notes

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