Dimethylformamide → HCID 86704009, compound

HRID 1773924Notes

Reaction equation

HRID 1773924 reaction equation
[CH:1]([C:4]1[N:5]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[N:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:3])[CH3:2].C(C1N=CN(CCC2C=CC=CC=2)C=1C1C=CC=CC=1)(C)C.[Li+].CC([N-]C(C)C)C.CN([CH:56]=[O:57])C>C1COCC1>[CH:1]([C:4]1[N:5]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:6]([CH:56]=[O:57])=[N:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 86704010HCID 86704010, compoundHCID 86704011HCID 86704011, compound

Product 1

HCID 86704009HCID 86704009, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of the mixture of 4-isopropyl-3-phenethyl-5-phenylimidazole and 5-isopropyl-3-phenethyl-4-phenylimidazole (example 243C) (1.2 g, 4.14 mmoles) in THF (15 mL) under argon is cooled to −78° C. A 2.0M LDA solution (2.2 mL, 4.4 mmoles) is added dropwise. After 30 minutes at −78° C., DMF (1.83 g, 25 mmoles) is added dropwise. The reaction mixture is allowed to reach 0° C., then it is quenched by adding a half-saturated NaHCO3 solution. The aqueous phase is extracted three times with AcOEt. The organic phase is washed with water, brine, dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (heptane:AcOEt) as eluent with a gradient from (1:0) to (8:1) to give 5-isopropyl-1-phenethyl-4-phenylimidazole-2-carbaldehyde.

Workup

  1. customto reach 0° C.
  2. customit is quenched
  3. additionby adding a half-saturated NaHCO3 solution
  4. extractionThe aqueous phase is extracted three times with AcOEt
  5. washThe organic phase is washed with water, brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent is removed under reduced pressure
  9. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-3cfd9cae1c8a483496acc756d281b3ab
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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