Acetaldehyde → Methyl 1-(1-hydroxyethyl)-3,3-dimethoxycyclobutanecarboxylate

Temperatur

0 °C

To a solution of diisopropylamine (3.2 mL, 22.67 mmol) in THF (45 mL) was added n-BuLi (2.69 M in hexane, 7.7 mL, 20.71 mmol) at −78° C. under argon. The mixture was stirred for 10 minutes at 0° C., then cooled to −78° C. and added a solution of methyl 3,3-dimethoxycyclobutanecarboxylate (3.0 g, 17.22 mmol) in THF (10 mL). The mixture was stirred for 30 minutes at −78° C., then added a solution of acetaldehyde (1.9 mL, 33.86 mmol) in THF (10 mL). The mixture was stirred for 30 minutes at −78° C., and water was added. The aqueous layer was extracted with EtOAc. Combined organic layers were washed with brine, dried over Na2SO4, filtered, and evaporated under reduced pressure to give methyl 1-(1-hydroxyethyl)-3,3-dimethoxycyclobutanecarboxylate (3.33 g).

1. temperaturecooled to −78° C.
2. stirringThe mixture was stirred for 30 minutes at −78° C.
3. stirringThe mixture was stirred for 30 minutes at −78° C.
4. extractionThe aqueous layer was extracted with EtOAc
5. washCombined organic layers were washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customevaporated under reduced pressure

ORD-Eintrag

ord-6bbb94ad91dc4247a6febf44a6d922aa

Quelldatensatz

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08975415B2