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

HRID 1685630

반응식

HRID 1685630 반응식
[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]

참가 물질

5

반응물 3

HCID 959522-ChloroethylbenzoateHCID 2734983Cesium bicarbonateHCID 5369209Monomethyl Fumarate

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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)+.

출처 및 근거

ORD 기록
ord-3a5f335c25d0443eb7f5789fa82b3bf3
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148414B2

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