Hydrochloric Acid → HCID 86602123, compound

Temperature

-78 °C

To a stirred mixture of 2-benzyl-α,α-dimethyl-2H-tetrazole-5-acetic acid, ethyl ester acetaldehyde (step 1 of Example 9) (6.14 g, 22.4 mmol) in dichloromethane (100 mL) at −78° C. was added DIBAL (1.0 M in toluene, 50.0 mL, 50.0 mmol). The resulting mixture was stirred at −78° C. for 4 h. To the reaction mixture was added DIBAL (1.0 M in toluene, 25.0 mL, 25.0 mmol) and the resulting mixture was stirred at −78° C. for 8 h. To the mixture were added 2 M aqueous HCl (100 mL) and saturated aqueous NH4Cl (20 mL). The organic layer was separated, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (10:1) to give 3.45 g (67%) of the title compound as a colorless oil.

1. stirringthe resulting mixture was stirred at −78° C. for 8 h
2. customThe organic layer was separated
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe resulting residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (10:1)

ORD record

ord-229fa18658b24a37b86fdb7ad6e34c7e

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07705020B2