Sulfuric Acid → (S)-tert-Butyl 2-chloropropanoate

Temperatur

0 °C

Prepared according to Wright et al. Tetrahedron Lett. 1997, 38, 7345. A 500 mL glass bomb was charged with magnesium sulfate (21.7 g, 181 mmol) and DCM (182 mL). To this suspension was added sulfuric acid (2.5 mL, 45 mmol), drop-wise with vigorous stirring. After 15 min of stirring, (S)-2-chloropropanoic acid (5.0 g, 45 mmol) was added followed by tert-butanol (21.6 ml, 226 mmol). The bomb was sealed and stirred at rt for 19 h, whereupon it was cooled to 0° C. and sodium bicarbonate (aq satd, 350 mL) was carefully added, at which point all solids had dissolved. The layers were separated and the aqueous layer was extracted with DCM (2×). The combined organics layers were washed with brine, dried over Na2SO4 and concentrated in vacuo (20° C. bath, 50 mBar) to afford the title compound (7.64 g, 96%) as a light yellow oil (93% purity). 1H NMR data was an identical match to the previously prepared enantiomer.

1. customPrepared
2. customThe bomb was sealed
3. stirringstirred at rt for 19 h, whereupon it
4. dissolutionhad dissolved
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with DCM (2×)
7. washThe combined organics layers were washed with brine
8. dry with materialdried over Na2SO4
9. concentrationconcentrated in vacuo (20° C. bath, 50 mBar)

ORD-Eintrag

ord-87e3fe566c49496bbd065ada9d49db33

Quelldatensatz

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09174978B2