Dimethyl Sulfoxide → 5,5-Dimethyl-1,3-dioxane-2-propionaldehyde

DMSO (10.2 ml, 0.14 mol) was added to a solution of oxalyl chloride (5.5 ml, 63.2 mmol) in methylene chloride (25 ml) at −78° C. After stirring for 15 min, a solution of 5,5-dimethyl-1,3-dioxane-2-propanol (Step 1) (10 g, 57.5 mmol) in methylene chloride (100 ml) was added over 10 min. The reaction was stirred for 1 hr and triethylamine (40 ml, 0.2 mol) was added. After stirring at −70° C. for 1 hr, the reaction mixture was warmed to room temperature and stirred for 2 hr. The reaction was quenched with water and extracted with methylene chloride. The organic fractions were washed with aqueous sodium bicarbonate and brine. After drying (Na2SO4), filtration and concentration, the crude compound was chromatographed (silica gel, hexane/ethyl acetate 7/3) to give 5,5-dimethyl-1,3-dioxane-2-propanal (6.1 g, 61%) as a colorless liquid: Anal Calc'd. for C9H16O3 0.2H2O: C, 61.48; H, 9.40. Found: C, 61.46; H, 9.24.

1. stirringThe reaction was stirred for 1 hr
2. stirringAfter stirring at −70° C. for 1 hr
3. stirringstirred for 2 hr
4. customThe reaction was quenched with water
5. extractionextracted with methylene chloride
6. washThe organic fractions were washed with aqueous sodium bicarbonate and brine
7. customAfter drying
8. filtration(Na2SO4), filtration and concentration
9. customthe crude compound was chromatographed (silica gel, hexane/ethyl acetate 7/3)

ORD record

ord-42f5453761704efcbab0d2cd61432de9

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07420061B2