Methanol → 3-Butyn-2-ol, 1-(4-fluorophenoxy)-, (2S)-

To a solution of (3S)-4-(4-fluorophenoxy)-3-(3′,5′-dinitrobenzoyl)oxy-1-butyne (10.35 g, 98% ee, 27.6 mmol) in THF (115 mL), was added methanol (115 mL) and K2CO3 (0.58 g). After stirring for 3.5 hours, the reaction mixture was quenched with acetic acid (2 mL). The solvents were evaporated and the resulting slurry was filtered and the solid was washed with ether. The filtrate was concentrated and the filtration/ether wash sequence was repeated. Concentration gave 4.02 g of (3S)-4-(4-fluorophenoxy)-3-hydroxy-1-butyne (98% ee), a compound of formula (BB); 1H NMR (CDCl3) δ 2.56 (s, 1H), 4.10 (m, 2H), 4.78 (m, 1H), 6.85 (m, 2H), 7.0 (m, 2H).

1. customthe reaction mixture was quenched with acetic acid (2 mL)
2. customThe solvents were evaporated
3. filtrationthe resulting slurry was filtered
4. washthe solid was washed with ether
5. concentrationThe filtrate was concentrated
6. filtrationthe filtration/ether
7. washwash sequence
8. concentrationConcentration

ORD record

ord-1705dce7ce274cc6a3352e093080056b

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06831186B2