Cesium bicarbonate → Methyl (methylethoxycarbonyloxy)ethyl (2E)but-2-ene-1,4-dioate

HRID 1624184Notes

Reaction equation

HRID 1624184 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+].Cl[CH2:16][CH2:17][O:18][C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20]>CN1C(=O)CCC1>[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([O:6][CH2:16][CH2:17][O:18][C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20])=[O:5]

Participants

5

Reactant 3

HCID 2734983Cesium bicarbonateHCID 5369209Monomethyl FumarateHCID 197651192-Chloroethyl propan-2-yl carbonate

Product 1

HCID 73295994Methyl (methylethoxycarbonyloxy)ethyl (2E)but-2-ene-1,4-dioateYield 91%

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 methylethyl (chloroethoxy)formate (0.70 g, 4.2 mmol) to afford 0.71 g (91% yield) of the title compound (40) after isolation and purification. 1H NMR (CDCl3, 400 MHz): δ 6.89 (d, J=15.6 Hz, 1H), 6.84 (q, J=5.2 Hz, 1H, superimposed), 6.82 (d, J=15.6 Hz, 1H, superimposed), 4.90 (heptet, J=6.2 Hz, 3H), 3.81 (s, 3H), 1.57 (d, J=5.2 Hz, 3H), 1.32 (d, J=6.2 Hz, 3H), 1.31 (d, J=6.2 Hz, 3H). MS (ESI): m/z 261.02 (M+H)+.

Sources & evidence

ORD record
ord-6fd86eee4b834073ab2a2b03f22b6923
Source dataset
uspto-grants-2014_07
Patent number
US08778991B2

Reaction notes

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