HCID 520648, compound → HCID 73295995, compound

HRID 1624185Notes

Reaction equation

HRID 1624185 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].C(=O)([O-])O.[Cs+].[CH3:15][CH:16]([CH3:23])[C:17]([O:19][CH2:20][CH2:21]Cl)=[O:18]>CN1C(=O)CCC1>[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([O:6][CH2:21][CH2:20][O:19][C:17](=[O:18])[CH:16]([CH3:23])[CH3:15])=[O:5]

Participants

5

Reactant 3

HCID 520648HCID 520648, compoundHCID 2734983Cesium bicarbonateHCID 5369209Monomethyl Fumarate

Product 1

HCID 73295995HCID 73295995, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Following general procedure A, methyl hydrogen fumarate (0.39 g, 3.0 mmol) in NMP (8 mL) was reacted with CsHCO3 (0.69 g, 3.6 mmol) and chloroethyl 2-methylpropanoate (0.63 g, 4.2 mmol) to afford 0.65 g (89% yield) of the title compound (42) after isolation and purification. 1H NMR (CDCl3, 400 MHz): δ 6.93 (q, J=5.2 Hz, 1H), 6.88 (d, J=16.0 Hz, 1H), 6.81 (d, J=15.6 Hz, 1H), 3.81 (s, 3H), 2.55 (heptet, J=6.8 Hz, 3H), 1.54 (d, J=5.2 Hz, 3H), 1.18 (d, J=6.8 Hz, 6H). MS (ESI): m/z 245.05 (M+H)+.

Sources & evidence

ORD record
ord-bfb8fe8e6f3145398016c3612833fbc6
Source dataset
uspto-grants-2014_07
Patent number
US08778991B2

Reaction notes

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