Ethane, 2-bromo-1,1-diethoxy- → 1,1,2-Triethoxyethane

Participants

Reaction Conditions

Reaction Steps

A sealed tube was charged with 2-bromo-1,1-diethoxy-ethane (3.82 mL, 25.4 mmol) and sodium ethoxide (16.44 g, 50.7 mmol). The tube was sealed, heated to 120° C. and stirred overnight. The sealed tube was cooled to room temperature and the contents are dissolved in DCM and washed with water twice. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to give 1,1,2-triethoxy-ethane, which was taken into the next step without further purification. A portion (1.00 g, 6.16 mmol) was dissolved in THF (4 mL) at 0° C. and 5M aqueous HCl (2.5 mL, 12.3 mmol) was added. The reaction mixture was left to stir at room temperature for 1.5 hrs. The mixture was taken up in DCM and washed with water once. The aqueous layer was extracted twice with DCM. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford ethoxy-acetaldehyde, which was taken into the next step with no further purification.

Provenance & Evidence