Tetrahydrofuran → HCID 22643415, compound

HRID 2414783Notes

Reaction equation

HRID 2414783 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[Na].C1COCC1.Cl[C:15]1[N:19]([C:20]([CH3:22])=[CH2:21])[C:18]2[CH:23]=[CH:24][CH:25]=[CH:26][C:17]=2[N:16]=1>O>[OH:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][O:7][C:15]1[N:19]([C:20]([CH3:22])=[CH2:21])[C:18]2[CH:23]=[CH:24][CH:25]=[CH:26][C:17]=2[N:16]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81051,5-PentanediolHCID 5360545Sodium2×HCID 14025026HCID 14025026, compound

Product 1

HCID 22643415HCID 22643415, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.3 g of 1,5-pentanediol and 0.4 g of sodium were stirred under nitrogen atmosphere for 30 minutes with heating. After the sodium disappeared, the reaction mixture was added dropwise with 30 ml of anhydrous THF containing 2.9 g of 2-chloro-1-isopropenylbenzimidazole and then refluxed for 8 hours. After cooling to room temperature, the mixture was added with water and extracted with ethyl acetate. The solvent was evaporated under reduced pressure and the resulting residue was purified by silica gel column chromatography (ethyl acetate) to obtain 2 g of the title compounds (yield: 51%).

Workup

  1. temperaturewith heating
  2. temperaturerefluxed for 8 hours
  3. extractionextracted with ethyl acetate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-ee4a71a094ca4a678a5eda074ba7e086
Source dataset
uspto-grants-2004_11
Patent number
US06815455B1

Reaction notes

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