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 1053981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1053981
[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

Komponenten

6

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b0126dfb271941899deb680e00948410
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394284B2

Notizen zur Reaktion

Wird geladen…