Tetrahydro-4H-pyran-4-one → HCID 10559661, compound

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Reaction Steps

Tetrahydropyran-4-one (4.34 g, 43.4 mmol) is treated with benzylmagnesium chloride (2 M in THF, 32.5 mL, 65.0 mmol) according to general procedure A. The crude product is filtered through silica gel, first with CH2Cl2, then with 1:1 hexane/EtOAc, to give alcohol 17 as a colorless oil (7.3 g, 87%) . 1H NMR (CDCl3) 7.40-7.15(m,5), 3.80-3.65(m,4), 2.77(s,2), 1.81(s,1), 1.80-1.70(m,2), 1.50-1.40(m,2); 3C NMR(CDCl3) 135.90, 130.53, 128.32, 126.74, 68.55, 63.65, 49.42, 37.46; MS(MW=192.3, CI/CH4, eE=70eV) m/z 193 (M+H)+, 191, 176, 175(base peak), 157, 145, 129, 119, 101, 92, 83, 71.

Provenance & Evidence