Aluminium lithium hydride → HCID 11244656, compound

To a cold (5° C.) solution of ethyl ({4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}oxy)acetate (190) (0.200 g, 0.53 mmol) in THF (10 mL) was added 1 M solution of LiAlH4 (1.3 mL, 2.5 mmol). The reaction mixture was stirred at that temperature for 0.5 h. Reaction mixture was quenched with EtOAc (5 mL) and stirred for an additional 10 min before pouring into 20% aqueous HCl (50 ml). The reaction mixture was extracted with EtOAc (3×50 mL) and the combined organics washed with brine (1×25 ml), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel using hexanes and EtOAc (4:1 to 3:2) as an eluent to afford 155 mg (86%) of compound 224 as a white solid. 1H NMR (300 MHz, CD3OD): δ 7.04 (d, J=8.7 Hz, 2H), 6.94 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 6.70 (d, J=8.4 Hz, 2H), 4.03 (t, J=5.1 Hz, 2H), 3.86 (t, J=5.1 Hz, 2H), 2.32 (d, J=4.5 Hz, 4H), 1.60 (br s, 8H). LCMS (ESI): m/z 337 (M−H)−.

1. customReaction mixture
2. customwas quenched with EtOAc (5 mL)
3. stirringstirred for an additional 10 min
4. additionbefore pouring into 20% aqueous HCl (50 ml)
5. extractionThe reaction mixture was extracted with EtOAc (3×50 mL)
6. washthe combined organics washed with brine (1×25 ml)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under reduced pressure
9. customThe crude product was purified by flash chromatography on silica gel

ORD record

ord-3463287e9131412ab2beffbc58dffe8e

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560589B2