Ammonia → 2-{[(6-Bromo-3-pyridinyl)oxy]methyl}-1,3-propanediol

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Reaction Steps

Silyl ether 185 (11.06 g, 22.5 mmol) was treated with a solution of 1% HCl in 95% EtOH (desilylation conditions described by Cunico et al., 1980) (200 mL), and the mixture was stirred at room temperature for 13 h. The resulting solution was cooled (CO2/acetone), neutralised by dropwise addition of 7M NH3 in MeOH (10 mL) with stirring, and then concentrated to dryness and the residue was chromatographed on silica gel. Elution with 0-3% MeOH/CH2Cl2 firstly gave foreruns, and then further elution with 5% MeOH/CH2Cl2 gave 2-{[(6-bromo-3-pyridinyl)oxy]methyl}-1,3-propanediol (186) (5.56 g, 94%) as a white solid: mp (CH2Cl2) 90-91° C.; 1H NMR (CDCl3) δ 8.07 (d, J=3.1 Hz, 1H), 7.36 (d, J=8.7 Hz, 1H), 7.12 (dd, J=8.7, 3.1 Hz, 1H), 4.15 (d, J=6.1 Hz, 1H), 3.95 (dt, J=10.8, 4.9 Hz, 1H), 3.92 (dt, J=10.8, 5.3 Hz, 1H), 2.24 (m, 1H), 1.99 (t, J=5.1 Hz, 2H). Anal. (C9H12BrNO3) C, H, N.

Provenance & Evidence