Hexane → methyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate

HRID 1713933

반응식

HRID 1713933 반응식
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH3:16][Si](C=[N+]=[N-])(C)C.CCCCCC.[N+](=C)=[N-]>CO.C(Cl)Cl>[Cl:1][C:2]1[CH:12]=[CH:11][C:5](/[CH:6]=[CH:7]/[C:8]([O:10][CH3:16])=[O:9])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14]

참가 물질

6

반응물 4

HCID 8058HexaneHCID 9550DiazomethaneHCID 167693TrimethylsilyldiazomethaneHCID 614919HCID 614919, 화합물

생성물 1

HCID 28818827methyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate수율 97%

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

실험 절차

To a solution of 4-chloro-3-nitrocinnamic acid in a mixture of methanol/DCM (1:1, v/v, 0.09 M), a 2 M solution of trimethylsilyl diazomethane in hexane (4 eq) was slowly added until the yellow color persisted, indicating an excess of diazomethane. The resulting mixture was evaporated. PE was added to the residue and the resultant precipitate was filtered and dried under vacuo to afford the title compound (97%) as a solid. 1H NMR (400 MHz; DMSO-d6, 300 K) δ 3.75 (s, 3H), 6.86 (d, J 16, 1H), 7.73 (d, J 16, 1H), 7.84 (d, J 8.4, 1H), 8.08 (d, J 8.4, 1H), 8.48 (s, 1H); MS (ES+) m/z 242 (M+H)+.

후처리

  1. customThe resulting mixture was evaporated
  2. additionPE was added to the residue
  3. filtrationthe resultant precipitate was filtered
  4. customdried under vacuo

출처 및 근거

ORD 기록
ord-9b3887cbe5a844a3b63d906cc37a2fe8
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795250B2

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