Dimethyl Sulfoxide → 1-{[(Tert-butyldimethylsilyl)oxy]methyl}cyclobutane-1-carbaldehyde

Temperature

-78 °C

To a round bottom flask was added DCM (5.0 mL) and oxalyl chloride (2.0 M solution in DCM, 1.36 mL, 2.71 mmol). The reaction mixture was cooled to about −78° C. To the solution was added a solution of DMSO (0.385 mL, 5.42 mmol) in DCM (1.0 mL). The mixture was stirred for about 15 min at about −78° C. and then a solution of (1-((tert-butyldimethylsilyloxy)methyl)cyclobutyl)methanol (0.500 g, 2.17 mmol, prepared using General Procedure AL with diethyl cyclobutane-1,1-dicarboxylate [Fluka], General Procedure AK with tert-butylchlorodimethylsilane) in DCM (1.0 mL) was added. The reaction mixture was allowed to stir for about 15 min and then TEA (1.82 mL, 13.0 mmol) was added. The reaction mixture was allowed to stir for about 15 min and then warmed to ambient temperature. The reaction mixture was quenched with water (25 mL) and was extracted with DCM (3×25 mL). The organics were combined, dried with MgSO4, filtered and concentrated in vacuo to give the title compound as a colorless oil (0.486 g, 98%): 1H-NMR (DMSO-d6) δ 9.71 (s, 1H), 3.87 (s, 2H), 2.27 (m, 2H), 1.93 (m, 4H), 0.90 (s, 9H), 0.08 (s, 6H).

1. stirringto stir for about 15 min
2. stirringto stir for about 15 min
3. temperaturewarmed to ambient temperature
4. customThe reaction mixture was quenched with water (25 mL)
5. extractionwas extracted with DCM (3×25 mL)
6. dry with materialdried with MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-82a43f9a0de64842a408624f5fc6d2ef

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188083B2