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 1053981Notes

Reaction equation

HRID 1053981 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b0126dfb271941899deb680e00948410
Source dataset
uspto-grants-2016_07
Patent number
US09394284B2

Reaction notes

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