HCID 11450791, compound → HCID 11290828, compound

To a solution of 211i (2.42 g, 7.02 mmol) in acetic acid (10 mL) was added dropwise sodium hypochlorite solution (1.76 mL, ca. 3.5 mmol) at 18° C. Additional sodium hypochlorite solution (3×1.0 mL, ca. 6.0 mmol) was added after 20, 40, and 60 min under monitoring by TLC. The reaction was quenched with 2-propanol (4 mL) and diluted with deionized water (100 mL). The reaction mixture was extracted with ethyl acetate (3×60 mL). The combined organic layers were washed with saturated NaHCO3 solution (3×60 mL), water (60 mL) and brine (60 mL), dried over anhydrous MgSO4, and concentrated in vacuo. Purification of the crude product (2.38 g) by column chromatography (silica gel, ethyl acetate/hexanes=1/1) gave 214i (0.83 g, 35%) as a colorless wax. 1H NMR (CDCl3): δ (ppm): 3.33 (s, 4 H), 2.41 (t, J=7.4, 4 H), 1.85 (br, 2 H), 1.62-1.45 (m, 4 H), 1.35-1.18 (m, 16 H), 0.87 (s, 12 H). 13C NMR (CDCl3): δ(ppm): 212.09, 72.10, 42.99, 38.75, 35.20, 30.48, 29.42, 24.05, 23.99, 23.82. HRMS (LSIMS, gly): Calcd for C21H43O3 (MH): 343.3212, found: 343.3208. HPLC: 96.4% pure.

1. customThe reaction was quenched with 2-propanol (4 mL)
2. additiondiluted with deionized water (100 mL)
3. extractionThe reaction mixture was extracted with ethyl acetate (3×60 mL)
4. washThe combined organic layers were washed with saturated NaHCO3 solution (3×60 mL), water (60 mL) and brine (60 mL)
5. dry with materialdried over anhydrous MgSO4
6. concentrationconcentrated in vacuo
7. customPurification of the crude product (2.38 g) by column chromatography (silica gel, ethyl acetate/hexanes=1/1)

ORD record

ord-c3312af49de942269f0bf3aa0a1a0cae

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642653B2