Tetrahydrofuran → HCID 18385711, compound

To a stirred solution of 2-methyl-3-butyn-2-ol (416 mg) and dry THF (30 ml) under argon and at −78° C., was added 1.6 M butyllithium in hexane (5 ml) dropwise over 10 minutes. 20 minutes later, p-methylthiobenzaldehyde (0.5 ml) was added dropwise to the reaction solution. Then the reaction solution was allowed to warm up to the ambient temperature by removing the cold bath. After stirring the reaction mixture for 2 hours, the reaction solvent was removed in vacuo, which was followed by neutralization with dilute aqueous HCl solution. The reaction mixture was then extracted with dichloromethane (50 ml×3), and the dichloromethane layer was washed with water (50 ml×1). The dichlomethane layer was concentrated in vacuo and the resulting residue was subjected to column chromatographic separation (hexane/ethyl acetate=1:1) to yield 724 mg of 1-{4-(methylthio)phenyl}-4-hydroxy-4-methyl-2-pentyn-1-ol. NMR: δ1.54 (s, 6H), 2.36 (s, 1H), 2.48 (s, 3H), 2.62 (d, 1H), 5.43(d, J=5.4 Hz, 1H), 7.25 (d, J=6.9 Hz, 2H), 7.43 (d, J=6.9 Hz, 2H).

1. customby removing the cold bath
2. customthe reaction solvent was removed in vacuo, which
3. extractionThe reaction mixture was then extracted with dichloromethane (50 ml×3)
4. washthe dichloromethane layer was washed with water (50 ml×1)
5. concentrationThe dichlomethane layer was concentrated in vacuo
6. customthe resulting residue was subjected to column chromatographic separation (hexane/ethyl acetate=1:1)

ORD record

ord-4269cda1f50b4257bbed7d2fa10a0270

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06492416B1