Cesium bicarbonate → HCID 73295996, compound

HRID 1624189Notes

Reaction equation

HRID 1624189 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+].[C:15]([O:23][CH2:24][CH2:25]Cl)(=[O:22])/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19]>CN1C(=O)CCC1>[C:4]([O:6][CH2:25][CH2:24][O:23][C:15](=[O:22])/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])(=[O:5])/[CH:3]=[CH:2]/[C:1]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 2734983Cesium bicarbonateHCID 5369209Monomethyl FumarateHCID 86639358HCID 86639358, compound

Product 1

HCID 73295996HCID 73295996, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Following general procedure A, methyl hydrogen fumarate (0.22 g, 1.7 mmol) in NMP (4 mL) was reacted with CsHCO3 (0.38 g, 1.9 mmol) and chloroethyl methyl (2E)but-2-ene-1,4-dioate (0.27 g, 1.4 mmol) to afford 0.068 g (17% yield) of the title compound (45) after purification by silica gel flash chromatography (Biotage) using a mixture of ethyl acetate (EtOAc) and hexanes (1:3). 1H NMR (CDCl3, 400 MHz): δ 7.03 (q, J=5.2 Hz, 1H), 6.90 (d, J=16.0 Hz, 1H), 6.82 (d, J=16.0 Hz, 1H), 3.82 (s, 3H), 1.60 (d, J=5.2 Hz, 3H).

Sources & evidence

ORD record
ord-74d9e14926fb45079bba292d5d90edbf
Source dataset
uspto-grants-2014_07
Patent number
US08778991B2

Reaction notes

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