1,8-Diazabicyclo(5.4.0)undec-7-ene → (E)-3-{1-[5-Chloro-2-(4-chloro-benzyloxy)-benzyl]-5-methyl-1H-pyrazol-3-YL}-acrylic acid methyl ester

HRID 536561ノート

反応式

HRID 536561 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[C:6]([CH:16]=1)[CH2:7][N:8]1[C:12]([CH3:13])=[CH:11][C:10](C=O)=[N:9]1.[Li+].[Cl-].C[C:29](P(OC)(O)=O)([C:31]([O-:33])=[O:32])[CH3:30].[CH2:39]1CCN2C(=NCCC2)CC1>CC#N>[CH3:39][O:33][C:31](=[O:32])/[CH:29]=[CH:30]/[C:10]1[CH:11]=[C:12]([CH3:13])[N:8]([CH2:7][C:6]2[CH:16]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[N:9]=1

参加物

6

反応物 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 53413272TrimethylphosphonoacetateHCID 866856891-[5-Chloro-2-(4-chloro-benzyloxy)-benzyl]-5-methyl-1H-pyrazole-3-carbaldehyde

生成物 1

HCID 68019133(E)-3-{1-[5-Chloro-2-(4-chloro-benzyloxy)-benzyl]-5-methyl-1H-pyrazol-3-YL}-acrylic acid methyl ester

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of aldehyde 5 (0.25 g, 0.65 mmol), LiCl (0.03 g, 1.21 mmol), trimethylphosphonoacetate (0.11 mL, 0.71 mmol) and DBU (0.19 mL, 1.21 mmol) in CH3CN (10 mL) was stirred under a N2 atmosphere at RT for 2 h. The reaction mixture was partitioned between 2 M HCl (15 mL) and EtOAc (20 mL). The organic layer was separated, washed with sat. NaHCO3 (15 mL), brine (15 mL), dried (Na2SO4) and the volatiles were removed in vacuo to give a crude ester 6, 0.31 g (99%).

後処理

  1. customThe reaction mixture was partitioned between 2 M HCl (15 mL) and EtOAc (20 mL)
  2. customThe organic layer was separated
  3. washwashed with sat. NaHCO3 (15 mL), brine (15 mL)
  4. dry with materialdried (Na2SO4)
  5. customthe volatiles were removed in vacuo

出典と根拠

ORDレコード
ord-9e17cd973a1b4e68ab3d248a348a095b
出典データセット
uspto-grants-2014_10
特許番号
US08859606B2

反応ノート

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