Ammonium Chloride → HCID 58677823, compound

HRID 747110

Reaction equation

HRID 747110 reaction equation
I[C:2]1[CH:14]=[CH:13][C:5]([C:6]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[Li]CCCC.[C:20]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=[O:28])([O:22][CH3:23])=[O:21].[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1COCC1>[CH2:9]([N:8]([CH2:11][CH3:12])[C:6]([C:5]1[CH:13]=[CH:14][C:2]([CH:27]([OH:28])[C:26]2[CH:25]=[C:24]([CH:31]=[CH:30][CH:29]=2)[C:20]([O:22][CH3:23])=[O:21])=[CH:3][CH:4]=1)=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 639145Methyl 3-formylbenzoateHCID 875218N,N-diethyl-4-iodobenzamideHCID 178418339Butyllithium

Product 1

HCID 58677823HCID 58677823, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Conditions

Temperature
-78 °C

Procedure

INTERMEDIATE 5 (2.8 g, 9.0 mmol) was dissolved in TBF (100 mL) and cooled to −78° C. under nitrogen atmosphere. Then n-BuLi (8.4 mL, 1.07 M solution in hexane, 9.0 mmol) was added dropwise during 10 min at −65 to −78° C. The solution was canulated into 3-carbomethoxybenzaldehyde (1.49 g, 9.1 mmol) in toluene/THF (approx. 1:1, 50 mL) at −78° C. NH4Cl (aq.) was added after 30 min. After concentration in vacuo, extraction with EtOAc/water, drying (MgSO4) and evaporation of the organic phase, the residue was purified by chromatography on silica (0-75% EtOAc/heptane) to give INTERMEDIATE 6 (1.5 g, 49%).

Workup

  1. concentrationAfter concentration
  2. extractionin vacuo, extraction with EtOAc/water
  3. customdrying
  4. custom(MgSO4) and evaporation of the organic phase
  5. customthe residue was purified by chromatography on silica (0-75% EtOAc/heptane)

Sources & evidence

ORD record
ord-645b609879f343c8b1c3ca3bd33f4fc0
Source dataset
uspto-grants-2008_07
Patent number
US07396834B2

Linked notes

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