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 1053981노트

반응식

HRID 1053981 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-b0126dfb271941899deb680e00948410
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394284B2

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