Dimethylformamide → HCID 67486330, compound

POCl3 (12.9 ml, 141.2 mmol) was added to DMF (10.9 ml, 141.2 mmol) at 0° C. The reaction was immediately warmed to ambient temperature and was stirred for 30 minutes. ((2,2-Diethoxyethoxy)methyl)benzene (10.6 g, 47.1 mmol) was added as a solution in 80 mL of chloroform. The solution was stirred at 75° C. for 3.5 hours. The solution was cooled, poured over ice water, and neutralized with Na2CO3. The residue was extracted with chloroform and the organic layer was dried with Na2SO4 and concentrated. The residue was re-dissolved in MeOH (450 mL). NaOMe (25% in MeOH, 58 ml, 253 mmol) was added followed by 2-hydrazinylethanol (10.6 g, 139 mmol). The reaction was stirred overnight at ambient temperature. The material was concentrated in vacuo followed by dilution with saturated NH4Cl solution. The material was extracted with EtOAc, dried (MgSO4), and concentrated. Flash chromatography of the crude material gave 2-(4-(benzyloxy)-1H-pyrazol-1-yl)ethanol (1.81 g, 13%).

1. stirringThe solution was stirred at 75° C. for 3.5 hours
2. temperatureThe solution was cooled
3. extractionThe residue was extracted with chloroform
4. dry with materialthe organic layer was dried with Na2SO4
5. concentrationconcentrated
6. dissolutionThe residue was re-dissolved in MeOH (450 mL)
7. stirringThe reaction was stirred overnight at ambient temperature
8. concentrationThe material was concentrated in vacuo
9. extractionThe material was extracted with EtOAc
10. dry with materialdried (MgSO4)
11. concentrationconcentrated

ORD record

ord-5dc3d39f83ed481683eb3a709afa60ac

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362037B2