Water → HCID 14716854, compound

Participants

Reaction Conditions

Reaction Steps

Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (2.0 M THF solution, 9.42 mL, 18.84 mmol) in dry THF (6.0 mL), 4-(cyclohexoxy)-benzoate (1.17 g, 4.71 mmol) in dry THF (30 mL) was added dropwise. The mixture was left to react at rt for 4 h, then at 0° C. H2O (0.70 mL), 3.0 M KOH solution (0.70 mL) and H2O (1.6 mL) were very slowly added. The mixture was stirred for 1 h at 0° C., filtered to remove the solid residue, and the organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness, affording the title compound (0.57 g, 59%), which was used in the next step without any further purification. 1H NMR (DMSO-d6): δ 1.21-1.47 (m, 5H), 1.49-1.57 (m, 1H), 1.64-1.77 (m, 2H), 1.87-1.95 (m, 2H), 4.25-4.33 (m, 1H), 4.40 (d, J=5.7 Hz, 2H), 5.00 (t, J=5.7 Hz, 1H), 6.87 (d, J=8.5 Hz, 2H), 7.19 (d, J=8.5 Hz, 2H).

Provenance & Evidence