Methyl 4-(chloromethyl)benzoate → HCID 70102981, compound

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Reaction Steps

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by methods F and G, alkylating with 4-(methoxycarbonyl)benzyl chloride, to afford the alcohol as a white solid in 65% yield, mp=94°-95° C.; 1H NMR (CDCl3) δ 8.00 (d, J=8.4 Hz, 2H), 7.30 (d, J=8.4 Hz, 2H), 6.95-7.04 (m, 2H), 6.89 (dt, J=2.1, 8.0 Hz, 1H), 6.77 (dd, J=7.8, 1.5 Hz, 1H), 5.20 (s, 2H), 4.86 (dd, J=5.4, 7.7 Hz, 1H), 3.82-3.96 (m, 5H with 3H singlet at δ 3.89), 2.16-2.37 (m, 3H, one of which is exchangeable). 13C NMR (CDCl3) δ 166.8, 166.5, 144.1, 141.1, 130.1 (CH), 129.4, 128.4, 126.3 (CH), 124.2 (CH), 122.8 (CH), 117.3 (CH), 115.2 (CH), 75.1 (CH), 58.7 (CH2), 52.0 (CH3), 45.1 (CH2), 33.1 (CH2). IR 3450-3500 (br), 1719, 1660 cm-1. MS 342 (MH+), 324 (M--OH)+, 310 (M--OMe)+. Anal. Calc'd. for C19H19NO5 : C, 66.85; H, 5.61; N, 4.10. Found: C, 66.48; H, 5.47; N, 3.97.

Provenance & Evidence