Water → 5-Dimethylamino-naphthalene-1-sulfonic acid 2,2,2-trifluoro-1-(4-methyldisulfanyl-phenyl)-ethyl ester

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Reaction Steps

2,2,2-Trifluoro-1-(4-methyldisulfanyl-phenyl)-ethanol (6) (12 mg, 0.047 mmol) and dansyl chloride (15 mg, 0.057 mmol) were dissolved in dry CH2Cl2 (0.2 mL). A solution of DABCO (63 mg, 0.56 mmol) dissolved in dry CH2Cl2 (0.1 mL) was added dropwise to the above solution. After 4 hours at room temperature, the reaction was poured into H2O (30 mL) and extracted with ethyl acetate (3×30 mL). The combined organic phases were washed with H2O (3×30 mL), followed by brine (1×30 mL) and then dried over Na2SO4. The organic phase was collected by filtration and concentrated by rotary evaporation. Flash chromatography on silica gel using 0-15% acetone/hexanes to yield Compound 1 as a yellow solid (6.5 mg, 28%). 1H NMR (400 MHz, CDCl3): δ 8.46 (d, J=8.5 Hz, 1H), 8.2 (d, J=8.7 Hz, 1H), 8.07 (d, J=7.3 Hz, 1H), 7.57 (t, J=7.9 Hz, 1H), 7.37 (t, J=8.2 Hz, 1H), 7.16 (d, J=7.2 Hz, 1H), 7.13 (d, J=8.4 Hz, 2H), 7.03 (d, J=8.3 Hz, 2H), 5.59 (q, J=6.3 Hz, 1H), 2.84 (s, 6H), 2.37 (s, 3H); 19F NMR (376 MHz, CDCl3): δ −76.3 (d, J=6.3 Hz). HRMS calc'd for C21H21F3NO3S3: 488.0636. found: 488.0647.

Provenance & Evidence