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

HRID 1626069

Reaction equation

HRID 1626069 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-4c8404c350b44d65a98cc2db6daeb07d
Source dataset
uspto-grants-2014_07
Patent number
US08785443B2

Linked notes

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