Water → HCID 14349143, compound

A mixture of 3-(6,6,6-trifluorohexanoyl)phenol (6.8 g, 27 mmol) and 2-chloromethylquinoline (4.4 g, 25 mmol) in DMSO (75 ml) containing 2N NaOH solution (14 ml) was stirred at room temperature overnight (13 hrs.). The dark reaction mixture was poured into water (200 ml) and the aqueous solution was extracted with ethyl acetate (4×30 ml). The organic extract was washed with 1N NaOH solution, water and brine and then dried over MgSO4. After removal of all volatiles, a dark liquid was obtained which solidified on standing (7.2 g). This solid was chromatographed (3% ethanol in toluene on silica gel) to obtain a beige color solid (4.5 g; mp 83°-4° C.), which was chromatographed again (15% acetone in hexanes on silica gel) to get a white solid (3.1 g; mp 86°-87° C.). This pure material was recrystallized from hexanes-acetone (trace) to leave the desired compound as a colorless, crystalline solid (2.4 g), mp 88°-88.5° C. (first crop; second crop mp 87°-88° C.).

1. customThe dark reaction mixture
2. extractionthe aqueous solution was extracted with ethyl acetate (4×30 ml)
3. extractionThe organic extract
4. washwas washed with 1N NaOH solution, water and brine
5. dry with materialdried over MgSO4
6. customAfter removal of all volatiles
7. customa dark liquid was obtained which
8. customThis solid was chromatographed (3% ethanol in toluene on silica gel)
9. customto obtain a beige color solid (4.5 g; mp 83°-4° C.), which
10. customwas chromatographed again (15% acetone in hexanes on silica gel)
11. customto get a white solid (3.1 g; mp 86°-87° C.)
12. customThis pure material was recrystallized from hexanes-acetone (trace)

ORD record

ord-1fa47b9d440942a2980d2107442f94c6

Source dataset

uspto-grants-1988_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04794188