Triethylamine → HCID 21844643, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL round bottomed flask was placed a solution of 6-(3-formylpropyl)-2-hydroxytetrahydropyran (153 mg, 0.89 mmol), DMAP (5 mg), and Et3N (0.4 mL) in CH2Cl2 (10 mL). The solution was cooled to 0° C., and tert-butyldimethylsilyl chloride (205 mg, 1.34 mmol) in CH2Cl2 (3 mL) was added dropwise. The reaction mixture was allowed to warm to room temperature overnight, and then the solvent was removed under reduced pressure. Ether was added and the organic layer was washed with saturated NH4Cl twice followed by brine, dried over anhydrous magnesium sulfate, and then concentrated in vacuo. The residue was submitted to column chromatography on silica gel to afford 6-(3-formylpropyl)-2-(tert-butyldimethylsiloxy)tetrahydropyran as a clear yellow oil (206 mg, 90% yield): 1H NMR (CDCl3) δ 0.09 (s, 3H), 0.10 (s, 3H), 0.89 (s, 9H), 1.19-1.73 (m, 10H), 2.43 (m, 2H), 3.34 (t, 1H, J=5.7 Hz), 4.63 (d, 1H, J=9 Hz), 9.74 (s, 1H); 13C NMR (CDCl3) δ -4.0, 18.14, 18.41, 22.21, 25.81, 30.61, 33.83, 35.25, 43.70, 75.70, 97.26, 202.63. HRMS [CI (CH4)] calcd for C15H29O3Si: 285.1886 (M-H,)+. Found: 285.1890 (Δ-1.4 ppm).

Provenance & Evidence