HCID 18428365, compound → HCID 11163443, compound

HRID 1276470Notes

Reaction equation

HRID 1276470 reaction equation
[Li]CCCC.Br[C:7](Br)=[CH:8][C:9]1[N:10]=[CH:11][N:12]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=1>C1COCC1>[C:27]1([C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:12]2[CH:13]=[C:9]([C:8]#[CH:7])[N:10]=[CH:11]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 18428365HCID 18428365, compoundHCID 178418339Butyllithium

Product 1

HCID 11163443HCID 11163443, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-BuLi (0.192 ml, 0.48 mmol) was added to a solution of 4-(2,2-dibromovinyl)-1-(triphenylmethyl)imidazole (108 mg, 0.22 mmol) in THF (5 ml) at -78° C. under N2. The reaction mixture was quenched by the addition of saturated ammonium chloride (50 ml) and extracted with ethyl acetate (75 ml). The ethyl acetate layer was washed with water (50 ml), separated, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by flash chromatography gave 2[1-triphenylmethyl-1H-imidazol-4yl]ethyne, which was deprotected with 2N HCL to give 18 mg of final product. ##STR77## 4-Ethynylimidazole (46) 1H-NMR (300 MHz, CD3OD): δ8.94 (s, 1H), 7.80 (s, 1H), 4.20 (s,1H); Mass Spectrum (Cl) m/e 93 (M+1).

Workup

  1. customThe reaction mixture was quenched by the addition of saturated ammonium chloride (50 ml)
  2. extractionextracted with ethyl acetate (75 ml)
  3. washThe ethyl acetate layer was washed with water (50 ml)
  4. customseparated
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography

Sources & evidence

ORD record
ord-60141b8f9b8941b1823941ecfe96ab5d
Source dataset
uspto-grants-2000_12
Patent number
US06166060

Reaction notes

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