Lithium hydroxide, monohydrate → Benzoic Acid

Temperature

0 °C

To a solution of (R)-1-methoxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxopropan-2-yl benzoate (14.2 g, 30.3 mmol) in tetrahydrofuran (80 mL) and methanol (80 mL) at 0° C. was added a solution of lithium hydroxide monohydrate (5.09 g, 121 mmol) in water (80 mL). The reaction was stirred at 0° C. for 1 h. The ice bath was removed and stirring continued at room temperature for 2 h. The reaction was concentrated, dissolved in water (5 mL), cooled to 0° C., and treated with 1M hydrochloric acid until mildly acidic. A non-solid ppt formed. The suspension was extracted with ethyl acetate (3×), which were washed with brine, dried over magnesium sulfate, and concentrated to give the crude hydroxy acid as an oil with white solid forming in it (probably residual benzoic acid) which was used without purification. Mass spec.: 349.34 (M−H)−.

1. customThe ice bath was removed
2. stirringstirring
3. waitcontinued at room temperature for 2 h
4. concentrationThe reaction was concentrated
5. dissolutiondissolved in water (5 mL)
6. temperaturecooled to 0° C.
7. additiontreated with 1M hydrochloric acid until mildly acidic
8. customA non-solid ppt formed
9. extractionThe suspension was extracted with ethyl acetate (3×), which
10. washwere washed with brine
11. dry with materialdried over magnesium sulfate
12. concentrationconcentrated
13. customto give the crude hydroxy acid as an oil with white solid

ORD record

ord-71b5509d0a724120ab4edfb7435d1904

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772244B2