m-Chloroperbenzoic acid → HCID 12716095, compound

To a solution of allylic alcohol 7 (5.0 g, 33.7 mmol) in dry CH2Cl2 (60 mL) at 0° C. was added m-chloroperbenzoic acid (8.7 g, 50.6 mmol) in small portions. The resulting solution was stirred for 8 h until complete consumption of starting materials (the progress of the reaction was monitored by TLC). The reaction mixture was quenched with water and the aqueous layer was extracted with CH2Cl2 (3×30 mL). The organic layer was washed with aq. 10% solution of NaHCO3 (15 mL). The combined organic layer was dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography over silica gel using petroleum ether/EtOAc (4:1) to give the corresponding epoxide 8 (4.8 g, 88%) as a viscous gum. IR: (CHCl3, cm−1): νmax 700, 991, 1028, 1055, 1106, 1452, 2921, 3404; 1H NMR (200 MHz, CDCl3): δ 2.88-2.99 (m, 3H), 3.17-3.23 (m, 1H), 3.57-3.72 (m, 1H), 3.85-3.95 (m, 1H), 7.18-7.34 (m, 5H); 13C NMR (50 MHz, CDCl3): δ 34.2, 67.1, 78.9, 87.5, 125.5, 127.5, 128.4, 140.8; Anal. Calcd for C10H12O2: C, 73.15; H, 7.37. Found: C, 73.25; H, 7.47%.

1. customThe reaction mixture was quenched with water
2. extractionthe aqueous layer was extracted with CH2Cl2 (3×30 mL)
3. washThe organic layer was washed with aq. 10% solution of NaHCO3 (15 mL)
4. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
5. customthe solvent was removed under reduced pressure
6. customThe crude product was purified by column chromatography over silica gel

ORD record

ord-ad80d9cf25514b4fb15ddeb9f9e1f424

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233943B2