Sodium Hydroxide → HCID 11194794, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl (2S,3S)-2-methyl-3-tetrahydropyranyloxybutanoate (4) (8.18 g, 35.56 mmol) at 0° C. was added dropwise to a stirred suspension of LiAlH4 (2.70 g, 71.12 mmol) in THF/toluene (2:1) (178 ml). The reaction mixture is stirred at 0° C. for 30 minutes, and then at room temperature for 30 minutes. The reaction is neutralized by means of the “Fieser treatment”; the reaction was treated by successively adding dropwise 2.7 ml of ice-cold water, 2.7 ml of a 15% aqueous NaOH solution, and 3×2.7 ml of ice-cold water. After having stirred for at least 30 minutes, the mixture is filtered on Celite. The precipitated aluminum salts were then washed with EtOAc. The solvent was evaporated, the residual oil was purified by means of flash chromatography on a silica gel column (heptane/EtOAc=5:1 and then 2:1) in order to obtain (2R,3S)-2-methyl-3-tetrahydropyranyloxybutanol (5) in the form of a colorless oil (6.59 g, 99%): 1H NMR (250 MHz, CDCl3) δ 4.69 to 4.67 (m, 0.5H); 4.58 to 4.56 (m, 0.5H); 3.98 to 3.43 (m, 5H); 1.80 to 1.48 (m, 7H); 1.29 (d, J=6.3 Hz, 1.5H); 1.18 (d, J=6.1 Hz, 1.5H); 0.95 (d, J=7.0 Hz, 1.5H); 0.94 (d, J=7.0 Hz, 1.5H); 13C NMR (50 MHz, CDCl3) δ 99.9; 97.4; 78.4; 74.9; 65.2; 64.2; 62.7; 41.2; 40.6; 31.3; 31.0; 25.3; 25.1; 20.7; 19.8; 18.9; 17.5; 14.0; 13.0; MS (CI) m/z 189 [M+H]+. HRMS calculated for C10H21O3 (M+H), 189.14906; found, 189.14755.

Provenance & Evidence