Ammonium Chloride → HCID 22507303, compound

Method 6 General Experimental: Magnesium (230.0 mmol, 5.6 g) in TBF (200 ml), under an argon atmosphere, was treated with 2-(2-bromoethyl)-1,3-dioxolane (200.0 mmol, 23.5 ml), slowly, keeping the internal temperature below 35° C. with the aid of an ice bath. After completion of the addition, the mixture was held at room temperature for an additional 1 h. 2-Trifluoromethyl benzaldehyde (100 mmol, 13.2 ml) in THF (100 ml) was cooled to −78° C. under an argon atmosphere, then treated with the freshly formed Grignard reagent prepared above. After completion of the addition, the solution was allowed to warm to room temperature, then held at room temperature overnight. The reaction mixture was then poured into saturated aqueous NH4Cl (200 ml), and extracted with ethyl acetate (2×150 ml). The combined organics were washed with brine (2×75 ml), then concentrated under reduced pressure to give 32.8 g of 3-[1,3]dioxolan-2-yl-1-(2-trifluoromethyl-phenyl)-propan-1-ol, which may be used without further purification. 1H NMR (CDCl3) δ7.78 (1H, d, J=7.7), 7.62-7.52 (2H, m), 7.34 (1H, t, J=7.6), 4.92 (1H, t, J=4.0), 4.00-3.81 (5H, m), 1.90-1.80 (4H, m).

1. customthe internal temperature below 35° C.
2. additionAfter completion of the addition
3. customprepared above
4. additionAfter completion of the addition
5. waitheld at room temperature overnight
6. extractionextracted with ethyl acetate (2×150 ml)
7. washThe combined organics were washed with brine (2×75 ml)
8. concentrationconcentrated under reduced pressure

ORD record

ord-b9a8ae4d97674f8484caf2e47b7126cc

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610730B2