Hydrochloric Acid → (R)-2-Methyl-2-trifluoromethoxymethyl-but-3-enoic acid

Temperature

5 °C

A solution of crude (R)-2-methyl-2-trifluoromethoxymethyl-but-3-enoic acid methyl ester (98 mg) in tetrahydrofuran (4 mL) was stirred at 5° C. under nitrogen. A solution of lithium hydroxide monohydrate (63 mg, 1.5 mmol) in water (1 mL) was added and the reaction mixture was stirred at 5° C. for 1 h and then at room temperature for 3 days. Water was added and the mixture was acidified to pH 2 with hydrochloric acid (2 M) and the mixture was extracted with diethyl ether. The organic extracts were combined and washed with brine. The organic solution was filtered through a hydrophobic frit and the filtrate was evaporated to afford the crude title compound (95 mg) as a clear oil which was used in the next step. LCMS (m/z) 197.1 [M−H], Tr=2.16 min.

1. waitat room temperature for 3 days
2. extractionthe mixture was extracted with diethyl ether
3. washwashed with brine
4. filtrationThe organic solution was filtered through a hydrophobic frit
5. customthe filtrate was evaporated

ORD record

ord-6cccb28b1e6845538c0ad7e1765485cb

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062092B2