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

HRID 1626067Notes

Reaction equation

HRID 1626067 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-4e643b9bf3dd497db1ecad354a97de12
Source dataset
uspto-grants-2014_07
Patent number
US08785443B2

Reaction notes

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