Diethyl Malonate → HCID 70843787, compound

HRID 1521663Notes

Reaction equation

[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:25]>CN(C)C=O.[Cl-].[NH4+]>[Cl:25][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([N+:22]([O-:24])=[O:23])[C:16]=1[CH2:15][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (1.8 g, 0.077 mol) was suspended in N,N-dimethylformamide (150 mL) at 0° C. Diethyl malonate (9.9 g, 0.0623 mol) was added in three portions and the resulting suspension was stirred at 0° C. for 10 min. A solution of 2-(bromomethyl)-1-chloro-3-nitrobenzene (147-1; 13 g, 0.0519 mol) in N,N-dimethylformamide (150 mL) was added drop wise. The reaction mixture was stirred for 45 min at 0° C., then diluted with saturated ammonium chloride and extracted with ethyl acetate (2×250 mL). The combined organics were dried over anhydrous sodium sulphate and concentrated to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 7.762-7.741 (d, J=8.4 Hz, 1H), 7.635-7.616 (d, J=7.6 Hz, 1H), 7.365-7.324 (t, J=8.4 Hz, 1H), 4.195-4.142 (q, J=7.2 Hz, 4H), 3.817-3.779 (t, J=7.6 Hz, 1H), 3.675-3.656 (d, J=7.6 Hz, 2H), 1.236-1.201 (t, J=7.2 Hz, 6H).

Workup

stirringThe reaction mixture was stirred for 45 min at 0° C.
extractionextracted with ethyl acetate (2×250 mL)
dry with materialThe combined organics were dried over anhydrous sodium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-45f72715f91a4a168ee92f8fdb3528d9
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073929B2

Reaction notes

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