Ethyl vinyl ether → HCID 22227318, compound

Temperature

0 °C

To a solution of ethyl vinyl ether (19.47 g, 270 mmol) in THF was added 106 mL of tert-butyl lithium (1.7 M, 180 mmol) dropwise at −78° C. The solution was warmed to 0° C. with an ice bath, stirred for another one hour and then re-cooled to −78° C. To this lithiated enol ether was added dropwise a solution of 5-methoxymethoxy-2-pentanone (13.16 g 90 mmol) in 10 mL of THF. The resulting mixture was stirred for one hour at −78° C. and one and a half hour at 0° C., and then slowly warmed up to room temperature. The reaction mixture was quenched with 70 mL of saturated NH4Cl aq. The organic layer was separated and the aqueous layer was extracted with 3×100 mL of diethyl ether. The combined organic layer was dried over Na2SO4 and concentrated via rotary evaporation to afford 2-ethoxy-3-hydroxy-6-methoxymethoxy-3-methyl-1-hexene in quantitative yield (19.4 g). The crude product was used in the subsequent reaction without further purification.

1. temperaturere-cooled to −78° C
2. stirringThe resulting mixture was stirred for one hour at −78° C. and one and a half hour at 0° C.
3. temperatureslowly warmed up to room temperature
4. customThe reaction mixture was quenched with 70 mL of saturated NH4Cl aq. The organic layer
5. customwas separated
6. extractionthe aqueous layer was extracted with 3×100 mL of diethyl ether
7. dry with materialThe combined organic layer was dried over Na2SO4
8. concentrationconcentrated via rotary evaporation

ORD record

ord-6aeac0c81f334bb497e651f3bf041e89

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07019453B2