Triethylamine → Ethyl 2-(((methylsulfonyl)oxy)methyl)cyclopropanecarboxylate

To a reaction solution of ethyl 2-(hydroxymethyl)cyclopropanecarboxylate (4-1) (577 mg; 4.0 mmol) with Et3N (1.1 mL; 8.0 mmol) and DMAP (49 mg; 0.4 mmol) in 12 mL of CH2Cl2 at 0° C. was added methanesulfonyl chloride (0.4 mL; 4.8 mmol). The resulting mixture of brown color suspension was stirred at 0° C. to room temperature under N2 for overnight. The reaction mixture was quenched with NaHCO3, then partitioned between CH2Cl2 (200 mL) and saturated NaHCO3 solution (50 mL); brine (50 mL). The organic layer was dried (Na2SO4), then filtered through silica gel pad, eluted with hexane:EtOAc/1:1. The filtrate was concentrated by vacuum to give 880 mg of ethyl 2-{[(methylsulfonyl)oxy]methyl}cyclopropanecarboxylate as a yellow oil (99% yield). 1H NMR (400 MHz, chloroform-D) δ ppm 0.91-1.02 (m, 1H) 1.26 (q, J=6.99 Hz, 3H) 1.29-1.36 (m, 1H) 1.63-1.74 (m, 1H) 1.79-1.92 (m, 1H) 3.02 (s, 3H) 3.99-4.24 (m, 4H).

1. additionThe resulting mixture of brown color suspension
2. customThe reaction mixture was quenched with NaHCO3
3. custompartitioned between CH2Cl2 (200 mL) and saturated NaHCO3 solution (50 mL)
4. dry with materialThe organic layer was dried (Na2SO4)
5. filtrationfiltered through silica gel pad
6. washeluted with hexane
7. concentrationThe filtrate was concentrated by vacuum

ORD record

ord-d7a4eee0c69447e4bcc32560d4047a8d

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858643B2