Water → Ethyl-m-nitrocinnamate

HRID 1256080

반응식

HRID 1256080 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[CH2:12]([O:14][C:15](=[O:25])[CH2:16]P(OCC)(OCC)=O)[CH3:13].[H-].[Na+].O>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:16][C:15]([O:14][CH2:12][CH3:13])=[O:25])[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 74493-NitrobenzaldehydeHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydride

생성물 1

HCID 94827Ethyl-m-nitrocinnamate수율 96.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-nitrobenzaldehyde (49 g, 295 mmol) and (diethoxy-phosphoryl)-acetic acid ethyl ester (72.74 g, 325 mmol) in DMF (300 ml) at 0° C. was added NaH (14.2 g, 354 mmol) portionwise and stirred for 1.5 hrs at r.t. The reaction mixture was poured into water to give colorless crystals, which were collected by filtration and washed with water and hexane to give the product ethyl 3-(3-nitrophenyl)acrylate (63 g, yield 96.6%). 1H NMR MeOD 400 MHz. δ 8.42-7.62 (m, 4H), 7.74-7.70 (d, 1H), 6.68-6.64 (d, 1H), 4.28-4.22 (m, 2H), 1.34-1.30 (m, 3H).

후처리

  1. customto give colorless crystals, which
  2. filtrationwere collected by filtration
  3. washwashed with water and hexane

출처 및 근거

ORD 기록
ord-bd0fdc0f03f3443c8d05728335aaed51
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461134B2

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