Sulfuric Acid → (S)-tert-Butyl 2-chloropropanoate
Reaction equation
S([O-])([O-])(=O)=O.[Mg+2].S(=O)(=O)(O)O.[Cl:12][C@@H:13]([CH3:17])[C:14]([OH:16])=[O:15].[C:18](O)([CH3:21])([CH3:20])[CH3:19].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:12][C@@H:13]([CH3:17])[C:14]([O:16][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15]Participants
Conditions
- Temperature
- 0 °C
Procedure
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.
Workup
- customPrepared
- customThe bomb was sealed
- stirringstirred at rt for 19 h, whereupon it
- dissolutionhad dissolved
- customThe layers were separated
- extractionthe aqueous layer was extracted with DCM (2×)
- washThe combined organics layers were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo (20° C. bath, 50 mBar)
Sources & evidence
- ORD record
- ord-87e3fe566c49496bbd065ada9d49db33
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174978B2
Reaction notes
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