Diethyl (ethoxymethylene)malonate → HCID 67267578, compound

HRID 598097Notes

Reaction equation

[C:1]1([CH3:23])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[N:14]=[C:13]([CH2:15][N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=1.C([Li])CCC.[CH3:29][CH2:30][O:31][CH:32]=[C:33]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[C:34]([O:36][CH2:37][CH3:38])=[O:35]>O1CCCC1>[CH2:17]([N:16]([CH2:20][CH2:21][CH3:22])[CH:15]([C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([C:2]2[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=2[CH3:23])[N:14]=1)[CH:32]([CH:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:39]([O:41][CH2:42][CH3:43])=[O:40])[O:31][CH2:30][CH3:29])[CH2:18][CH3:19]

Participants

Conditions

Temperature: -78 °C

Procedure

N-[(6-mesitylpyridin-2-yl)methyl]-N-propylpropan-1-amine (0.71 g, 2.29 mmol), was dissolved in tetrahydrofuran (15 mL). The solution was cooled to −78° C. and n-butyllithium (2.5M, 1.0 mL, 2.51 mmol) was added drop wise. After 0.5 h, diethyl ethoxymethylene malonate (0.48 mL, 2.40 mmol) was added. The reaction was removed from the dry ice bath and allowed to warm to room temperature. The mixture was quenched with water, extracted with ether, dried over sodium sulfate, filtered and concentrated. Flash chromatography gave 0.65 g (59% yield) of an isomeric mixture of the title compound.

Workup

customThe reaction was removed from the dry ice bath
temperatureto warm to room temperature
customThe mixture was quenched with water
extractionextracted with ether
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-3c2d3cb0627a41b185d0b53f9ae56b40
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897607B2

Reaction notes

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