Sodium Thiosulfate → Ethyl 6-oxohexanoate

To a flask containing ethyl 6-hydroxyhexanoate (4.07 mL, 25.0 mmol) in CH2Cl2 (25 mL) was added TEMPO (391 mg, 2.50 mmol) followed by iodobenzene diacetate (8.86 g, 27.5 mmol). The reaction was stirred 2 hours and then diluted with CH2Cl2 (100 mL). Saturated aqueous solution of Na2S2O3 (100 mL) was added and extracted with CH2Cl2 (3×50 mL). The combined organics were washed with saturated aqueous NaHCO3 (150 mL) and brine (150 mL), dried over Na2SO4, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (20-40% Et2O/pentanes) to provide the title compound, which was identical to the reported literature compound. (See: Taber, D. F.; Teng, D. (2002) J. Org. Chem., 67: 1607.)

1. extractionextracted with CH2Cl2 (3×50 mL)
2. washThe combined organics were washed with saturated aqueous NaHCO3 (150 mL) and brine (150 mL)
3. dry with materialdried over Na2SO4
4. concentrationconcentrated in vacuo
5. customThe resulting residue was purified by silica gel chromatography (20-40% Et2O/pentanes)

ORD record

ord-bfc297eb862847fda78ae0a92e6bc697

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07265249B2