Dimethylformamide dimethyl acetal → Ethyl 2-(3-fluoro-4-nitrobenzoyl)-3-(dimethylamino)acrylate

HRID 2197521

반응식

HRID 2197521 반응식
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[F:9][C:10]1[CH:11]=[C:12]([C:19](=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17]>C1(C)C=CC=CC=1>[F:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:19]([C:20](=[CH:3][N:4]([CH3:5])[CH3:6])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:26]

참가 물질

4

반응물 2

HCID 78373Dimethylformamide dimethyl acetalHCID 57955348Ethyl 3-(3-fluoro-4-nitrophenyl)-3-oxopropanoate

생성물 1

HCID 66640928Ethyl 2-(3-fluoro-4-nitrobenzoyl)-3-(dimethylamino)acrylate수율 100%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
50 °C

실험 절차

N,N-Dimethylformamide dimethyl acetal (100 g, 810 mmol) was added dropwise (10 min) to a cooled (0° C.) solution of ethyl 3-(3-fluoro-4-nitrophenyl)-3-oxopropanoate (138 g, 540 mmol) in toluene (540 mL). The reaction was warmed (50° C.) for 2.5 h and then the volatiles were evaporated under reduced pressure to afford the desired product (167 g, 100%), which was sufficiently pure (>95% by NMR) to proceed without further purification. 1H NMR (300 MHz, DMSO-d6) δ 8.24-8.29 (m, 1H), 7.92 (s, 1H), 7.60-7.74 (m, 1H), 7.58-7.62 (m, 1H), 3.97 (q, J=7.0 Hz, 2H), 3.44 (s, 3H), 2.81 (s, 3H), 0.99 (t, J=7.0 Hz, 3H); ES-MS m/z 310.9 (MH)+; HPLC RT (Method B) 2.87 min.

후처리

  1. customthe volatiles were evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-5231fb07d87f437eab152022000a8cb1
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338594B2

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