2-Methyl-3-butyn-2-ol → HCID 59354753, compound

Temperature

-78 °C

To a pre-cooled, −78° C. stirred solution of 2-methylbut-3-yn-2-ol (4.3 g, 0.04 mol) in dry THF (150 mL) n-BuLi (39.9 mL, 0.03 mol, 1.6 M in hexane) was added dropwise over 10 minutes under an inert atmosphere. The mixture was stirred for 30 min at −78° C., and then a solution of 4-methoxy-benzaldehyde (5 g, 0.037 mol) in dry THF (30 mL) was added to reaction mixture and stirring was continued for an additional 40 min at −78° C. The reaction mixture was then quenched with a saturated NH4Cl solution and extracted with EtOAc (2×100 mL). The combined organic layers were washed with water (100 mL) and brine (100 mL), dried over Na2SO4, filtered and concentrated in vacuo to obtain crude material. The crude material was purified via silica gel column chromatography eluting with 5% EtOAc in hexanes to afford 1-(4-methoxyphenyl)-4-methylpent-2-yne-1,4-diol (6.3 g, 78%) as an oil.

1. additionwas added dropwise over 10 minutes under an inert atmosphere
2. stirringstirring
3. waitwas continued for an additional 40 min at −78° C
4. customThe reaction mixture was then quenched with a saturated NH4Cl solution
5. extractionextracted with EtOAc (2×100 mL)
6. washThe combined organic layers were washed with water (100 mL) and brine (100 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto obtain crude material
11. customThe crude material was purified via silica gel column chromatography
12. washeluting with 5% EtOAc in hexanes

ORD record

ord-8d46434ea4d441d6bcc425fc847ea200

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933074B2