Tetrahydrofuran → HCID 86684882, compound

HRID 238384Notes

Reaction equation

HRID 238384 reaction equation
CC(C)([O-])C.[K+].O1CCCC1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=1.Cl[C:22]1[N:26]([CH3:27])[N:25]=[CH:24][C:23]=1[CH:28]=[O:29]>O>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][O:18][C:22]2[N:26]([CH3:27])[N:25]=[CH:24][C:23]=2[CH:28]=[O:29])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 133974-Chlorobenzyl alcoholHCID 151450195-Chloro-1-methyl-1H-pyrazole-4-carbaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 86684882HCID 86684882, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under cooling in an ice bath, potassium tert-butoxide (217 mg) was added to a tetrahydrofuran (2.8 mL) solution of 4-chlorobenzyl alcohol (217 mg), and the obtained solution was then stirred for 20 minutes. Under cooling in an ice bath, 5-chloro-1-methyl-1H-pyrazol-4-carbaldehyde (200 mg) was added to the reaction solution, and the obtained solution was then stirred for 3 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=80:20 to 60:40), so as to obtain the title compound (127 mg) in the form of a colorless oily substance.

Workup

  1. temperatureUnder cooling in an ice bath
  2. temperatureUnder cooling in an ice bath
  3. stirringthe obtained solution was then stirred for 3 hours
  4. extractionthe obtained mixture was then extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated saline
  6. dry with materialwas then dried over anhydrous magnesium sulfate
  7. concentrationfollowed by vacuum concentration
  8. customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=80:20 to 60:40)

Sources & evidence

ORD record
ord-9b2c2c571e6947398b7fbb17e346055c
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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