Sodium hydride → 2-(2-Methyl-allyloxy)-pent-4-enoic acid ethyl ester

Temperature

0 °C

To a cold (0° C.) stirred suspension of NaH (55% dispersion in oil, 227.9 mg, 5.2 mmol, 1.3 eq) in THF (20 mL) was added drop wise a solution of 2-hydroxy-pent-4-enoic acid ethyl ester (0.576 g, 4.0 mmol) in THF (20 mL) and stirred for 1 h. The reaction mixture was then treated with 3-bromo-2-methylpropene (0.81 g, 6.0 mmol, 0.61 mL), slowly warmed up to rt, and stirred for 1 h. It was carefully quenched with saturated NH4Cl solution. Reaction mixture was extracted with EtOAc (3×20 mL) organic solution was washed with brine, dried (Na2SO4), concentrated. Purification of the residue on silica gel column chromatography using 5% EtOAc-Hexane furnished 2-(2-methyl-allyloxy)-pent-4-enoic acid ethyl ester (0.521 g, 66%) as oil.

1. stirringstirred for 1 h
2. temperatureslowly warmed up to rt
3. stirringstirred for 1 h
4. customIt was carefully quenched with saturated NH4Cl solution
5. customReaction mixture
6. extractionwas extracted with EtOAc (3×20 mL) organic solution
7. washwas washed with brine
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated
10. customPurification of the residue on silica gel column chromatography

ORD record

ord-3980e6e15dec443680c99ed38b5a74b0

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08357718B2