Sodium Thiosulfate → HCID 86656572, compound

Temperature

50 °C

A 1.0 M tetrahydrofuran solution of borane tetrahydrofuran complex (15.0 mL, 15.0 mmol) was slowly added to a tetrahydrofuran solution (7 mL) of ethyl 4-methyl-4-pentenoate (6.07 g, 42.7 mmol) at 0° C. The solution was heated to 50° C. for one hour then cooled to ambient temperature. Anhydrous methanol (1 mL) was added to quench the excess hydride, followed by sodium acetate (43 mL, 43.0 mmol) in methanol. To this reaction mixture at ambient temperature was added slowly iodine monochloride (1.5 mL, 30 mmol). The reaction mixture was stirred for two hours and poured into water (50 mL). Saturated aqueous sodium thiosulfate was added, and the mixture was extracted with diethyl ether (3×100 mL). The combined organic extracts were washed with brine, dried (magnesium sulfate), and concentrated in vacuo. The residue was purifed by column chromatography on silica gel, eluting with 0-30% ethyl acetate/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.00 (d, J=5.5 Hz, 3H), 1.25 (t, J=7.0 Hz, 3H), 1.45-1.60 (m, 2H), 1.70-1.78 (m, 1H), 2.30 (t, J=7.1 Hz, 2H), 3.15 (dd, J=4.7, 9.4 Hz, 1H), 3.21 (dd, J=6.3, 9.4 Hz, 1H), 4.12 (q, J=7.1 Hz, 2H).

1. temperaturethen cooled to ambient temperature
2. customto quench the excess hydride
3. extractionthe mixture was extracted with diethyl ether (3×100 mL)
4. washThe combined organic extracts were washed with brine
5. dry with materialdried (magnesium sulfate)
6. concentrationconcentrated in vacuo
7. washeluting with 0-30% ethyl acetate/hexanes

ORD record

ord-8aa062a63f7b4d3cab422b13c781f3e8

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947664B2