反应详情

1.00 g (3.4 mmol) of (5-tert-butyl-2-methyl-4-thiocyanato-phenoxy)acetic acid methyl ester prepared in Example KKK was combined with 3.16 g (20 mmol) dithiothreitol (DTT) in a solution of 10 mL 0.02 M K2PO4 buffer and 40 mL of EtOH. The reaction was refluxed overnight, then cooled and partially concentrated. After dilution with water, the mixture was extracted with EtOAc, and the organic layer washed with saturated aqueous brine, dried (Na2SO4) and concentrated. The residue was chromatographed on silica gel eluting with 3:1 hexanes:EtOAc, to give the title compound. 1H NMR (CDCl3) δ 1.44 (s, 9 H), 2.19 (s, 3 H), 3.46 (s, 1 H), 3.80 (s, 3 H), 4.62 (s, 2 H), 6.76 (s, 1 H), 7.06 (s, 1 H).

1. temperatureThe reaction was refluxed overnight
2. temperaturecooled
3. concentrationpartially concentrated
4. extractionAfter dilution with water, the mixture was extracted with EtOAc
5. washthe organic layer washed with saturated aqueous brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated
8. customThe residue was chromatographed on silica gel eluting with 3:1 hexanes