Methallyl alcohol → HCID 66955648, compound

Temperature

0 °C

A solution of 2-methyl-2-propen-1-ol (120) (2.34 mL, 27.8 mmol) in anhydrous DMF (10 mL, then 2×2 mL to rinse) was added to a suspension of 60% NaH (1.32 g, 33.1 mmol) in anhydrous DMF (10 mL) under N2 at 0° C. and the mixture was stirred at 0° C. for 30 min. 4-(Trifluoromethoxy)benzyl bromide (5.1 mL, 31.9 mmol) was added and the mixture was stirred at room temperature for 21 h. The resulting mixture was added to ice/aqueous NaHCO3 (200 mL) and extracted with 25% EtOAc/petroleum ether (2×200 mL) and 50% EtOAc/petroleum ether (3×200 mL). The extracts were washed with water (200 mL), the volatile solvents were removed, and the residual oil was chromatographed on silica gel. Elution with petroleum ether firstly gave foreruns, then further elution with 0-15% CH2Cl2/petroleum ether gave 1-{[(2-methyl-2-propenyl)oxy]methyl}-4-(trifluoromethoxy)benzene (121) (6.57 g, 96%) as an oil that was used directly in the next step; 1H NMR (CDCl3) δ 7.37 (dt, J=8.7, 2.3 Hz, 2H), 7.19 (br d, J=8.0 Hz, 2H), 5.00 (m, 1H), 4.94 (m, 1H), 4.48 (s, 2H), 3.94 (s, 2H), 1.77 (s, 3H).

1. stirringthe mixture was stirred at room temperature for 21 h
2. extractionextracted with 25% EtOAc/petroleum ether (2×200 mL) and 50% EtOAc/petroleum ether (3×200 mL)
3. washThe extracts were washed with water (200 mL)
4. customthe volatile solvents were removed
5. customthe residual oil was chromatographed on silica gel
6. washElution with petroleum ether firstly gave foreruns
7. washfurther elution with 0-15% CH2Cl2/petroleum ether

ORD record

ord-594d4322df7d4471b4d1b3df5e3b86ca

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293734B2