Hydrogen Peroxide → HCID 11171416, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) solution of 11 (14.9 g, 80.8 mmol) in THF (250 mL) was added K-Selectride (potassium tri-sec-butylborohydride) (95.0 mmol, 1.0 M in THF). After addition was complete, the mixture was allowed to warm to −50° C. and stirred for an additional 4 h, whereupon the reaction was complete by TLC. The reaction was quenched by addition to 2.2 M NaH2PO4/K2HPO4 buffer (300 mL, pH =7). This was cooled (0° C.) and 30% hydrogen peroxide (42 mL, 370 mmol) was added and the mixture was allowed to stir overnight. The layers were separated and the aqueous layer was extracted with ethyl acetate (4×200 mL). The combined organics were washed with brine (300 mL), 1.0 M sodium sulfite (300 mL), dried (MgSO4) and the volatiles were removed in vacuo to yield an oil which was further purified by flash chromatography (12.48 g, 83% yield). Rf 0.35 (ethyl acetate/hexane 3:7); 1H NMR (300 MHz, CDCl3) δ 4.45-4.54 (m, 1H), 4.10 (q, J=7.2, 2H), 2.34-2.44 (m, 1H), 2.00-2.30 (b, 1H), 1.26-1.91 (m, 7H), 1.22 (t, J=7.2, 3H), 0.89 (d, J=6.4, 3H); 13C NMR (75 MHz, CDCl3) δ 176.1, 65.4, 60.0, 45.1, 35.8, 33.9, 32.0, 27.6, 20.2, 14.2; MS (EI) m/z 186 (M+, 3), 168 ([M-H2O]+, 37), 141 ([M-OCH2CH3]+, 25), 130 (12), 95 (100), 73 (27), 55 (34); [α]D−27.4° (c=1.10, CH2Cl2). Analysis calcs'd for C10H18O3: C, 64.49; H, 9.74. Found: C, 64.19; H, 9.62.

Provenance & Evidence