Dimethyl Sulfoxide → 1-(((Tert-butyldimethylsilyl)oxy)methyl)cyclopropane-1-carbaldehyde

Temperature

-70 °C

To a stirred solution of DMSO (6.9 mL, 0.097 mol) in anhydrous DCM (90 mL) at −70° C. was added oxalyl chloride (4.20 mL, 0.0486 mol). After stirring for 10 min. at −70° C., a solution of [1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methanol (7.011 g, 0.03240 mol) in anhydrous DCM (30 mL) was added via cannula. The resulting milky mixture was slowly warmed to −55° C. over 45 min. DIPEA (34.0 mL, 0.194 mol) was added. The resulting mixture was stirred for 5 min. at −55° C., and then the cooling bath was removed and the reaction mixture was allowed to warm to RT. The reaction was then quenched with saturated aqueous NaHCO3 (150 mL) and extracted with DCM (2×). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was purified by Combiflash chromatography eluting with 0-10% EtOAc/hexanes to afford the desired product as a colorless oil (4.558 g, 66% yield).

1. temperatureThe resulting milky mixture was slowly warmed to −55° C. over 45 min
2. stirringThe resulting mixture was stirred for 5 min. at −55° C.
3. customthe cooling bath was removed
4. temperatureto warm to RT
5. customThe reaction was then quenched with saturated aqueous NaHCO3 (150 mL)
6. extractionextracted with DCM (2×)
7. washThe combined organic layers were washed with brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe resulting residue was purified by Combiflash chromatography
12. washeluting with 0-10% EtOAc/hexanes

ORD record

ord-a31dd94b3304489db4db2711a03299fd

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07998959B2