Formaldehyde → HCID 20364904, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 17 (100 mg, 0.55 mmol) and paraformaldehyde (17 mg, 0.55 mmol) in EtOAc (10 mL), boron trifluoride etherate (70 μL, 0.55 mmol) was added and the reaction mixture was stirred at 23° C. for 4 h. The organic phase was washed with a saturated solution of NaHCO3, dried and the solvent was removed. The residue was purified by flash-chromatography eluting with a 1:4 mixture of EtOAc and hexanes to afford 84 mg (78%) of O-benzyl-1,3-dioxan-5-ol as a colourless oil. The above compound was dissolved in EtOAc (3 mL), Pd/C was added and the resulting suspension was stirred at rt under a hydrogen atmosphere. After 12 h, the catalyst was filtered off, the filtrate was evaporated in vacuo and the residue (39 mg, 100%) was used in the next step without further purification: 1H NMR (CDCl3) δ 4.93 (d, J=6.3 Hz, 1H), 4.76 (d, J=6.3 Hz, 1H), 3.94-3.84 (m, 4H), 3.64-3.61 (m, 1H), 2.78 (bs, 1H). 13C NMR (CDCl3) δ 94.0, 71.7, 64.1.

Provenance & Evidence