Hydrochloric Acid → HCID 13831435, compound

Temperature

2.5 °C

Under argon (Ar), lithium aluminum hydride (LiAlH4) (35.21 g, 0.98 mol) in 2.2 L of dry ether was placed in a 5-liter three-necked flask equipped with reflux condenser, dropping funnel, and mechanical stirrer under dry Ar. The mixture was cooled to 0-5° C., and a solution of 3 (185 g, 0.87 mol) in 1 L of ether was added dropwise. After the addition, the stirred mixture was allowed to slowly come to room temperature and stirred for 16-18 hr until no starting material could be detected by HPLC. The mixture was again cooled in an ice bath and excess hydride was carefully decomposed by addition of 6N HCl (750 mL). Stirring was continued overnight until the solution became a clear, light yellow color. The reaction mixture was extracted with 2×500 mL ethyl ether, and the combined ether layers were then washed with 2×700 mL of water and 500 mL of brine. The ether was evaporated, and the residue was dissolved in 700 mL of CH2Cl2 and dried over MgSO4. After filtration, the organic solvent was removed in vacuo to yield 159 g of a yellow oil in 95% yield. HPLC retention time 4.1 min, Bp 70° C. at 0.7 mm Hg. The reaction is shown as follows:

1. customequipped
2. temperaturewith reflux condenser
3. additionAfter the addition
4. customto slowly come to room temperature
5. temperatureThe mixture was again cooled in an ice bath
6. stirringStirring
7. waitwas continued overnight until the solution
8. extractionThe reaction mixture was extracted with 2×500 mL ethyl ether
9. washthe combined ether layers were then washed with 2×700 mL of water and 500 mL of brine
10. customThe ether was evaporated
11. dissolutionthe residue was dissolved in 700 mL of CH2Cl2
12. dry with materialdried over MgSO4
13. filtrationAfter filtration
14. customthe organic solvent was removed in vacuo

ORD record

ord-ef8f12e60b8347aba885a58789e82318

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158667B2