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

HRID 1713933

反応式

HRID 1713933 の反応式
[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]

参加物

6

反応物 4

HCID 8058HexaneHCID 9550DiazomethaneHCID 167693TrimethylsilyldiazomethaneHCID 614919HCID 614919、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-9b3887cbe5a844a3b63d906cc37a2fe8
出典データセット
uspto-grants-2010_09
特許番号
US07795250B2

関連ノート

読み込み中…