Cesium bicarbonate → HCID 46179452, compound

HRID 1624183Notes

Reaction equation

HRID 1624183 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][CH2:22][CH3:23])=[O:20]>CN1C(=O)CCC1>[C:4]([O:6][CH2:16][CH2:17][O:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:5])/[CH:3]=[CH:2]/[C:1]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 2734983Cesium bicarbonateHCID 5369209Monomethyl FumarateHCID 12238111ethyl (chloroethoxy)formate

Product 1

HCID 46179452HCID 46179452, compoundYield 85.3%

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 ethyl (chloroethoxy)formate (0.64 g, 4.2 mmol) to afford 0.63 g (85% yield) of the title compound (39) after isolation and purification. 1H NMR (CDCl3, 400 MHz): δ 6.89 (d, J=15.6 Hz, 1H), 6.82 (d, J=15.6 Hz, 1H), 6.84 (q, J=5.6 Hz, 1H), 4.23 (q, J=7.2 Hz, 3H), 3.81 (s, 3H), 1.58 (d, J=5.6 Hz, 3H), 1.32 (t, J=7.2 Hz, 3H). MS (ESI): m/z 247.01 (M+H)+.

Sources & evidence

ORD record
ord-72d7709c5f274a22a7682a5d7ee74b1c
Source dataset
uspto-grants-2014_07
Patent number
US08778991B2

Reaction notes

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