Methanol → HCID 59465835, compound

Temperature

75 °C

A mixture of 1-Methyl 2-(4-fluoro-1H-indol-1-yl)propanoate (21.3 g, 91 mmol), 1 N aq. NaOH (150 mL), and methanol (150 mL) was heated to 75° C. overnight. The volatiles were removed by evaporation under reduced pressure at 50° C. and ethyl acetate (250 mL) and water (200 mL) were added to the residue. The layers were separated and the aqueous layer was acidified with concentrated HCl to pH<1. The acidified layer was extracted with ethyl acetate (1×200 mL, 1×50 mL) and the combined extracts were washed with brine (100 mL), dried over sodium sulfate, filtered, and evaporated to dryness under reduced pressure at 50° C. to obtain the desired acid as a yellow oil (16.8 g, 76 mmol, 84% yield). 1H-NMR (300 MHz, CDCl3): δ 7.12-6.99 (m, 2H), 6.83-6.77 (m, 2H), 6.63-6.62 (m 1H), 1.92 (s, 6H).

1. customThe volatiles were removed by evaporation under reduced pressure at 50° C.
2. additionethyl acetate (250 mL) and water (200 mL) were added to the residue
3. customThe layers were separated
4. extractionThe acidified layer was extracted with ethyl acetate (1×200 mL, 1×50 mL)
5. washthe combined extracts were washed with brine (100 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customevaporated to dryness under reduced pressure at 50° C.

ORD record

ord-7e23591273534615a16d98a278baff91

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309587B2