Hydrochloric Acid → HCID 86654323、化合物

HRID 888565

反応式

HRID 888565 の反応式
[CH2:1]([O:3][C:4](=[O:16])[C:5]([C:14]#[N:15])=[CH:6][C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)[CH3:2].ClC1C=CC([Mg][Br:25])=CC=1.[ClH:26].[C:27]1(C)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:1]([O:3][C:4](=[O:16])[C:5]([C:30]1[CH:31]=[CH:32][C:27]([Br:25])=[CH:28][CH:29]=1)([C:14]#[N:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:26])=[CH:9][CH:8]=1)[CH3:2]

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 367501Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoateHCID 178478191HCID 178478191、化合物

生成物 1

HCID 86654323HCID 86654323、化合物収率 91%

反応条件

温度
85 °C

実験手順

A solution of 3-(4-bromo-phenyl)-2-cyano-acrylic acid ethyl ester (1.5 g, 5.36 mmol) in dry toluene (12 ml) was added dropwise to 4-chlorophenylmagnesium bromide (0.5 M solution in tetrahydrofuran, 6.96 ml, 6.96 mmol) at 0° C. The reaction mixture was heated to 85° C. for 3 hours, poured onto ice, acidified with 1N HCl and extracted with ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and concentrated, the crude product was purified over flash silica chromatography eluting with petroleum ether to ethyl acetate/petroleum ether (5:95) to afford the desired product (1.91 g, 91% yield). LC/MS: (PS-A2) Rt 3.78 [M+H]− 391.93.

後処理

  1. additionpoured onto ice
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe crude product was purified over flash silica chromatography
  8. washeluting with petroleum ether to ethyl acetate/petroleum ether (5:95)

出典と根拠

ORDレコード
ord-3e3e21ab170d41c7a5c51f7e0b7c237d
出典データセット
uspto-grants-2012_08
特許番号
US08247576B2

関連ノート

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