Pentane → HCID 12129626, compound

HRID 1348884Notes

Reaction equation

HRID 1348884 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[Si](CC)(CC)CC.C([Li])(C)(C)C.CCCCC.[C:24]([C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1)#[N:25]>C1COCC1>[OH:31][CH:30]([C:6]1[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=1)[C:29]1[CH:32]=[CH:33][C:26]([C:24]#[N:25])=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 8003PentaneHCID 660424-CyanobenzaldehydeHCID 11117116HCID 11117116, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 12129626HCID 12129626, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-methyl-2-(triethylsilyl)-1H-imidazole (3.35 g, 17.08 mmol) in THF (50 mL) at −78° C. was treated dropwise with 2.5M tert-butyllithium in pentane (22.4 mL, 17.1 mmol), stirred for 30 minutes, treated dropwise with a solution of 4-cyanobenzaldehyde (2.04 g, 15.56 mmol) in THF (10 mL), and stirred for 1 hour. The mixture was quenched with methanol (4 mL), treated with 1N HCl (40 mL), warmed to room temperature, adjusted to pH 12 with 30% NaOH, and extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was triturated with 4:1 hexanes/ethyl acetate to provide 2.95 g (89%) of the desired product. MS (DCI/NH3) m/z 214 (M+H)+; 1H NMR (CDCl3) δ 7.67 (d, 2H), 7.53 (d, 2H), 7.40 (s, 1H), 6.67 (s, 1H), 5.95 (s, 1H), 3.53 (s, 3H).

Workup

  1. stirringstirred for 1 hour
  2. customThe mixture was quenched with methanol (4 mL)
  3. additiontreated with 1N HCl (40 mL)
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was triturated with 4:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-6846cdb51f8c4409bd8f2cdde07de9d5
Source dataset
uspto-grants-2007_05
Patent number
US07211595B2

Reaction notes

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