2-(Dimethylamino)ethanol → HCID 9870903, compound

Participants

Reaction Steps

The product of Example 1 (10.71 g), triphenylphosphine (9.63 g), and dimethylaminoethanol (3.27 g) were dissolved in tetrahydrofuran (60 ml). To the resultant solution diisopropyl azodicarboxylate (7.43 g) was added dropwise over 30 min with stirring on ice. After completion of dropwise addition of the solution, the mixture was further stirred for one hour at room temperature and the solvent was removed under reduced pressure. The residue was purified through two steps: NH silica gel column chromatography (solvent=hexane:ethyl acetate=3:1,) and silica gel column chromatography (solvent=hexane:ethyl acetate=1:1 and chloroform:methanol=10:1). The resultant product was re-crystallized from ether-hexane, to thereby obtain the target product (7.42 g) in the form of crystals. Mp.: 99° C.; 1H-NMR(270 MHz, CDCl3) δ: 7.65 (2H, d, J=8.58 Hz), 7.41 (2H, d, J=8.58 Hz), 7.25 (2H, d, J=8.91 Hz), 7.18 (1H, m), 6.87 (2H, d, J=8.91 Hz), 6.72 (1H, d, J=8.25 Hz), 6.47 (2H, m), 5.78 (1H, brs), 4.08 (3H, m), 3.51 (2H, m), 3.12 (1H, m), 2.42 (1H, m), 2.22 (1H, m), 2.20 (6H, s).

Provenance & Evidence