Lithium Hydroxide → HCID 14358757, compound

To a solution of (R)-(+)-Methyl 2-(tert-butyldimethylsilyloxy)propanoate (5.26 g, 24.09 mmol) in THF (283 mL) at 0° C. was added an aqueous LiOH solution (0.2 M, 283 mL). After stirring at room temperature for 4 hr, the reaction mixture was concentrated to 50% of the original volume and extracted with petroleum ether (2×50 mL). The ether extracts were combined and extracted with a saturated aqueous NaHCO3 solution (50 mL). The aqueous layers were combined and acidified to pH 3 to 4 with an aqueous KHSO4 solution (1M, 100 mL). The aqueous solution was extracted with petroleum ether (3×250 mL) and the combined organic layers were dried over Na2SO4 and concentrated to afford 5.45 g of (R)-(+)-2-(tert-butyldimethylsilyloxy)propanoic acid as colorless oil (100%, product contains ˜10% water). 1H NMR (CDCl3): δ 4.29 (q, 1H, J=6.8 Hz, —CH), 1.38 (d, 3H, J=6.8 Hz, —CH3), 0.86 (s, 9H, Si—(CH3)3), 0.07 (s, 3H, Si—CH3), 0.06 (s, 3H, Si—CH3).

1. concentrationthe reaction mixture was concentrated to 50% of the original volume
2. extractionextracted with petroleum ether (2×50 mL)
3. extractionextracted with a saturated aqueous NaHCO3 solution (50 mL)
4. extractionThe aqueous solution was extracted with petroleum ether (3×250 mL)
5. dry with materialthe combined organic layers were dried over Na2SO4
6. concentrationconcentrated

ORD record

ord-6c2103f3150e4a27b23b8c6fffb1a2db

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08168648B2