3-Hydroxybenzaldehyde → 3-Prop-2-ynyloxy-benzaldehyde

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Reaction Conditions

Reaction Steps

Potassium tert-butoxide (6.16 g, 0.055 mole), 3-hydroxybenzaldehyde (6.1 g, 0.05 mole), and dry dimethylformamide (DMF, over Na2SO4 ; 30 mL) were stirred briefly at 25° C., and then propargyl bromide (6.6 g, 0.055 mole) was added in 30 mL of dry DMF according to the method of F. Albericio et al., "Preparation and Application of the5-(4-(9-Fluorenylmethyloxycarbonyl)-Aminomethyl-3,5-Dimethoxyphenoxy)-ValericAcidHandle for the Solid Phase Synthesis of C-Terminal Peptide Amides under Mild Conditions," J. Org. Chem. vol. 55, pp. 3730-3743 (1990). The reaction mixture was heated to 110° C. for 8 h, and the solvent was then removed under high vacuum. Ethyl acetate was added, inorganic salts were removed by filtration, and the organic extract was washed sequentially with water, 2 M NaOH, and saturated aqueous NaCl. The organic phase was dried overnight (MgSO4), and the solvent was removed to yield a yellow liquid that was purified by silica gel chromatography using hexane-ethyl acetate (8.5:1.5) as the eluting solvent. Yield: 6.5 g (81%). 1H NMR (CDCl3): d 2.54 (t, 1H, CH), 4.73 (t, 2H,--OCH2 --), 7.2-7.48 (m, 4H, Aromatics), 9.96 (s, 1H, CHO). GC-MS (m/z): M+ =160.

Provenance & Evidence