Cesium bicarbonate → HCID 46179452, compound

HRID 1626066Notes

Reaction equation

HRID 1626066 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-b32f653cf7004ee5b9d5033201b1f866
Source dataset
uspto-grants-2014_07
Patent number
US08785443B2

Reaction notes

Loading…