2-Chloroethylbenzoate → Methyl phenylcarbonyloxyethyl(2E)but-2-ene-1,4-dioate

HRID 1624186Notes

Reaction equation

HRID 1624186 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])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN1C(=O)CCC1>[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([O:6][CH2:25][CH2:24][O:23][C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:22])=[O:5]

Participants

5

Reactant 3

HCID 959522-ChloroethylbenzoateHCID 2734983Cesium bicarbonateHCID 5369209Monomethyl Fumarate

Product 1

HCID 46179454Methyl phenylcarbonyloxyethyl(2E)but-2-ene-1,4-dioateYield 24%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Following general procedure A, methyl hydrogen fumarate (0.42 g, 3.3 mmol) in NMP (6 mL) was reacted with CsHCO3 (0.69 g, 3.6 mmol) and chloroethyl benzoate (0.55 g, 3.0 mmol) to afford 0.2 g (24% yield) of the title compound (43) after purification by silica gel flash column chromatography (Biotage) using a mixture of ethyl acetate (EtOAc) and hexanes (1:8) as eluent. 1H NMR (CDCl3, 400 MHz): δ 8.08-8.02 (m, 2H), 7.63-7.56 (m, 1H), 7.49-7.42 (m, 2H), 7.21 (q, J=5.2 Hz, 1H), 6.92 (d, J=16.0 Hz, 1H), 6.85 (d, J=16.0 Hz, 1H), 3.81 (s, 3H), 1.69 (d, J=5.2 Hz, 3H). MS (ESI): m/z 278.99 (M+H)+.

Sources & evidence

ORD record
ord-708ee49b318d4d3eae5e8997ca6ab977
Source dataset
uspto-grants-2014_07
Patent number
US08778991B2

Reaction notes

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