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After filtration and removal of the solvent, the residue was chromatographed on silica gel (petroleum ether 60 90 °C:ethyl acetate = 3 1) to afford the product (30, 143 mg, 52%% yield) as a yellow oil.
Solvent was removed to yield the product (2.55 g, 91% yield) as a yellow oil without the need for further purification.
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The yellow-orange solution was concentrated to yield 5 a as a yellow solid.
3-Ethoxysalicylaldehyde (1.66 g), 2-aminoethanol (0.61 g), (81% yield) as yellow crystals (from ethanol); mp 88-90°C 88-90°C
The combined fractions were evaporated to dryness to yield 1 as a yellow oil (92 mg, 59%).
The residue was purified by chromatography using 10% EtOAc in heptane to yield 42 as a yellow solid.
The residue was purified by chromatography using 5% EtOAc in heptane to yield 39 as a yellow semi-solid.
After removal of the solvent under reduced pressure, the residue was chromatographed on silica gel (dichloromethane:MeOH NH3 H2O = 300 10 1) to afford the product (25, 0.82 g, 96%% yield) as a pale yellow syrup.
After removal of the solvent under reduced pressure, the residue was chromatographed on silica gel (petroleum ether 60 90 °C:ethyl acetate = 7 1) to afford the product (28a, 789 mg, 95%% yield) as a pale yellow syrup.
3-Hydroxycyclohexanone was obtained in 56% yield as a light yellow oil.
The product was dried under high vacuum to give the pure amine 14 (131 mg) in 78 % yield as a pale yellow solid.
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