Tetrahydrofuran → HCID 12137115, compound

HRID 1005951Notes

Reaction equation

HRID 1005951 reaction equation
C1COCC1.CC(C)([O-])C.[K+].[CH2:12]([OH:18])[CH2:13][CH2:14][CH2:15][CH2:16][OH:17].Cl[C:20]1[N:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:23]=[N:22][N:21]=1>O>[OH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:18][C:20]1[N:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:23]=[N:22][N:21]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81051,5-PentanediolHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 23665647Potassium tert-butoxide

Product 1

HCID 12137115HCID 12137115, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 ml of THF solution containing 225 mg of potassium t-butoxide was added with 0.6 g of 1,5-pentanediol and 0.36 g of 5-chloro-1-phenyl-tetrazole and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with water and extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane) to obtain 0.4 g of the title compound (yield: 81%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-60233b08b750468c89a62074e023aca4
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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