Triethylamine → 3,3-Diethoxy-1-propene

A solution of diol (Molecule 2.1) (1.5 g, 7.8 mmol) in 7.5 ml of dry DMF was treated with acrolein dimethyl acetal (4.62 ml, 39 mmol) and PTSA.H2O (0.371 g, 1.95 mmol). After stirring for 24 h at room temperature the reaction was stopped by addition of 1 ml of Et3N and poured out in 200 ml of H2O. The aqueous phase was extracted with toluene (3×100 ml) and the combined organics were washed once with brine (100 ml) and dried over MgSO4. Column chromatography of the residue over silica gel (cyclohexane/ethyl acetate: 85/15) afforded Molecule 2.2 (FIG. 4) as white crystals (1.306 g, 5.67 mmol, 73%).

1. extractionThe aqueous phase was extracted with toluene (3×100 ml)
2. washthe combined organics were washed once with brine (100 ml)
3. dry with materialdried over MgSO4

ORD record

ord-cc18b665322d4ac88e0828688dee6840

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07534871B2