Water → 5-tert-Butyl4-dimethylthiocarbamoyloxy-2-methyl-benzoic acid methyl ester

To a solution of 5-tert-butyl-4-hydroxy-2-methylbenzoic acid methyl ester from Example BBB (15.1 g, 68 mmol) in DMF (150 mL) was added NaH (3.3 g of a 60% dispersion, 82 mmol), and the mixture was stirred at room temperature for 1 hour. N,N-Dimethylthiocarbamoyl chloride (10.1 g, 82 mmol) was added all at once; the reaction mixture was stirred at 55° C. for 36 hours and then cooled to room temperature. H2O (200 mL) was added, and the solution was extracted with EtOAc. The combined extracts were washed with 1N NaOH, 1N HCl, and brine. The organic phase was dried (MgSO4) and concentrated. The residue was chromatographed on silica gel, eluting with 6:1 hexane:EtOAc, to give the title compound. 1H NMR (CDCl3) δ 1.37 (s, 9 H), 2.55 (s, 3 H), 3.39 (s, 3 H), 3.49 (s, 3 H), 3.89 (s, 3 H), 6.90 (s, 1 H), 8.01 (s, 1 H).

1. stirringthe reaction mixture was stirred at 55° C. for 36 hours
2. temperaturecooled to room temperature
3. extractionthe solution was extracted with EtOAc
4. washThe combined extracts were washed with 1N NaOH, 1N HCl, and brine
5. dry with materialThe organic phase was dried (MgSO4)
6. concentrationconcentrated
7. customThe residue was chromatographed on silica gel
8. washeluting with 6:1 hexane

ORD-Eintrag

ord-0cb51f7cb1ec4ae7baa7b157a4eb3c52

Quelldatensatz

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06046355