Dimethyl Sulfoxide → 2-(4,4-Dimethyl-chroman-7-yl)-heptanal

Temperature

-78 °C

To a solution of oxalyl chloride (0.15 mL) in 9 mL of dichloromethane at −78° C. was added 0.19 mL of DMSO. The mixture was stirred at −78° C. for 5 minutes and then a solution of 2-(4,4-dimethyl-chroman-7-yl)-heptan-1-ol (0.22 g, 0.79 mmole, from Example 1) in 3 mL of dichloromethane was added. The mixture was stirred at −78° C. for 15 minutes then 0.56 mL of triethylamine was added. Stirring was continued at −78° C. for another 15 minutes then at room temperature for two hours. The reaction mixture was quenched by the addition of 20 mL of water, extracted with three 20 mL portions of dichloromethane and the combined organic extracts were washed with two 20 mL portions of water and 20 mL of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes) to afford 0.16 g of 2-(4,4-dimethyl-chroman-7-yl)-heptanal as a colorless oil.

1. stirringThe mixture was stirred at −78° C. for 15 minutes
2. stirringStirring
3. waitwas continued at −78° C. for another 15 minutes
4. waitat room temperature for two hours
5. customThe reaction mixture was quenched by the addition of 20 mL of water
6. extractionextracted with three 20 mL portions of dichloromethane
7. washthe combined organic extracts were washed with two 20 mL portions of water and 20 mL of saturated aqueous sodium chloride solution
8. dry with materialThe organic phase was dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto give a yellow oil
12. customThe product was purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes)

ORD record

ord-21e3cb5d0319455c89be1e5b801f79ef

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354931B2