Methanol → (2S)-2-[(tert-butyldimethylsilyl)oxy]propanal

Temperature

-78 °C

To a solution of (S)-ethyl 2-(tert-butyldimethylsilyloxy)propanoate (6.3 g, 27.1 mmol) in CH2Cl2 (22 mL) was added 54.2 mL of DIBAL (1.0 M in CH2Cl2, 54.2 mmol) over 20 min at −78° C. After stirring for 2 h at −78° C., methanol (3 mL) was added to the solution at the same temperature. The mixture was allowed to warm to RT and saturated aqueous potassium sodium tartrate (60 mL) was added to the solution. The resulting mixture was vigorously stirred for 3 h. The mixture was extracted with dichloromethane (30 mL×2), and the combined extracts were washed with brine (20 mL), dried over sodium sulfate, and concentrated in vacuo. The residue was distilled under vacuum (bp 50-52° C., 0.5 mmHg) to afford 2.5 g (49%) of (S)-2-(tert-butyldimethylsilyloxy)propanal: 1H NMR (400 MHz, CHLOROFORM-d) δ 9.59 (d, J=1.3 Hz, 1H), 4.07 (dq, J=6.9, 1.3 Hz, 1H), 1.26 (d, J=6.9 Hz, 3H), 0.93 (s, 9H), 0.08 (s, 3H), 0.07 (s, 3H).

1. temperatureto warm to RT
2. stirringThe resulting mixture was vigorously stirred for 3 h
3. extractionThe mixture was extracted with dichloromethane (30 mL×2)
4. washthe combined extracts were washed with brine (20 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. distillationThe residue was distilled under vacuum (bp 50-52° C., 0.5 mmHg)

ORD record

ord-44461aaa173d49b597a090696c6336e9

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729263B2