Water → (R)-1-(3-Tert-butyloxycarbonylphenyl)ethylmethanesulfonyl Ether

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Reaction Steps

(R)-1-(3-Tert-butyloxycarbonylphenyl)ethanol (3.28 mmol) was dissolved in CH2Cl2 (10 mL), diisopropylethylamine (4.92 mmol) added and the resultant solution cooled to 0° C. This mixture was stirred as methanesulfonyl chloride (3.94 mmol) was added dropwise. After 45 min the mixture was poured into water and extracted 3× with diethyl ether. The organic extracts were combined, washed with brine, dried (MgSO4) and concentrated under reduced pressure to yield 1.01 g of an oil which was used with out further purification. 1H NMR (500 MHz, CDCl3): δ 8.03 (m, 1H); 8.01 (m, 1H); 7.60 (m, 1H); 7.48 (t, J=7.6 Hz, 1H); 5.80 (q, J=6.6 Hz, 1H); 2.81 (s, 3H); 1.76 (d, J=6.6 Hz, 3H); 1.63 (s, 9H).

Provenance & Evidence