Chloromethyl Methyl Ether → HCID 11845755, compound

To a solution of 21a (3.60 g, 16.6 mmol) in methanol (40 mL) was added sodium borohydride (640 mg, 16.6 mmol) at 0° C., and the mixture was stirred at room temperature for 1 h. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue were added dichloromethane (50 mL), diisopropylethylamine (3.5 mL, 20 mmol) and chloromethyl methyl ether (1.5 mL, 20 mmol) at 0° C., and the reaction mixture was stirred at room temperature overnight. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (15:1 hexane/ethyl acetate) to give 22a (2.99 g, 2 steps 68%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ (ppm) 3.04 (t, J=6.7 Hz, 2H), 3.31 (s, 3H), 3.77 (t, J=6.7 Hz, 2H), 4.62 (s, 2H), 6.82 (td, J=8.2, 3.2 Hz, 1H), 7.04 (dd, J=9.4, 2.9 Hz, 1H), 7.48 (dd, J=8.8, 5.3 Hz, 1H).

1. extractionthe mixture was extracted with ethyl acetate
2. washThe organic layer was washed with brine
3. dry with materialdried over anhydrous sodium sulfate
4. customThe solvent was removed under reduced pressure
5. stirringthe reaction mixture was stirred at room temperature overnight
6. extractionthe mixture was extracted with chloroform
7. washThe organic layer was washed with brine
8. dry with materialdried over anhydrous sodium sulfate
9. customThe solvent was removed under reduced pressure
10. customThe residue was purified by silica gel column chromatography (15:1 hexane/ethyl acetate)

ORD record

ord-89a34ebd582d4e268ed84f88dd9c99d3

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106031B2