N-Formylmorpholine → 4-(1,3-Dioxolan-2-yl)benzaldehyde

Temperature

-78 °C

To a tetrahydrofuran (100 mL) solution of 2-(4-bromo-phenyl)-1,3-dioxolane (8 g, 34.9 mmol) was added dropwise n-butyl lithium (19.6 mL, 2.67 M hexane solution, 52.4 mmol) at −78° C. After 1 hour of stirring at −78° C., N-formylmorpholine (4.42 g, 38.4 mmol) was added to the mixture, and stirred for 3 hours at the same temperature. This mixture was partitioned into diethyl ether and water. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (6.3 g). This compound was used in the subsequent reaction without being purified.

1. stirringstirred for 3 hours at the same temperature
2. customThis mixture was partitioned into diethyl ether and water
3. customThe organic layer was separated
4. washwashed with saturated aqueous sodium chloride
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under a reduced pressure

ORD record

ord-e59778493b1b4ac5a4d97d104eccfdee

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08153662B2