4-Chlorobenzaldehyde → (4-Chlorophenyl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol

Temperature

-30 °C

Analogous to the general method described in J. Org. Chem. 2004, 69, 8115, and Chem. Pharm. Bull, 1997, 1145. To a 2-necked flask containing 1-methyl-1H-1,2,3-triazole (1.00 g, 12.0 mmol, Intermediate 42, step a) was added THF (75 mL) and the solution was cooled between −40 to −20° C. To this colorless homogeneous solution was added n-BuLi (2.5 M in hexanes, 5.0 mL, 11.4 mmol) dropwise which afforded a dark brown viscous mixture. After stirring at 0° C. for 1 hours, a THF (10 mL) solution of 4-chlorobenzaldehyde (1.60 g, 11.4 mmol) was introduced and the reaction mixture began to be stirred freely and remained brownish. After 3 hours the reaction mixture was quenched by pouring into a saturated solution of NH4Cl and the aqueous portion was extracted with EtOAc (4×50 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give a brown oil which solidified upon standing. The crude material was triturated with Et2O to provide the title compound as a brown solid.

1. customafforded a dark brown viscous mixture
2. stirringto be stirred freely
3. customAfter 3 hours the reaction mixture was quenched
4. additionby pouring into a saturated solution of NH4Cl
5. extractionthe aqueous portion was extracted with EtOAc (4×50 mL)
6. washThe combined organics were washed with brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customto give a brown oil which
11. customThe crude material was triturated with Et2O

ORD record

ord-a7ddef2d8ca84253bd66dc996dd293cb

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309222B2