Ethyl Acetate → HCID 12960802, compound

Temperature

-75 °C

15.8 g. (77 mmol) of ethyl Z-2-fluoro-4,4-dimethoxy-3-methyl-2-butenoate was dissolved in 250 ml. of hexane in a 500 ml. round-bottomed flask fitted with a thermometer, argon inlet and dropping funnel. The resulting mixture was cooled to -75° C. and 63.5 ml. of di-isobutylaluminum hydride (1.45 equivalent of hydrogen) were added slowly thereto. The reaction mixture was stirred for 1 hour. Ethyl acetate (8.8 g., 100 mmol) was added thereto and the reaction mixture was allowed to come to -30° C. A mixture of 20 g. of sodium sulfate containing 3.6 g. of water was added thereto and stirring continued for 1 hour at 25°-35° C. The resulting material was twice filtered through celite and evaporated on a rotary evaporator at 31° C. (in glassware which had been rinsed with 8 N ammonium hydroxide and dried) to yield Z-2-fluoro-3-methyl-4,4-dimethoxy-2-buten-1-al obtained (approximately 10 g.). An inert gas atmosphere was maintained during all workup operations.

1. customround-bottomed flask fitted with a thermometer, argon inlet
2. customto come to -30° C
3. additionA mixture of 20 g
4. stirringstirring
5. waitcontinued for 1 hour at 25°-35° C
6. filtrationThe resulting material was twice filtered through celite
7. customevaporated on a rotary evaporator at 31° C.
8. wash(in glassware which had been rinsed with 8 N ammonium hydroxide and dried)

ORD record

ord-a64c71096f1c4f499b083470915aa142

Source dataset

uspto-grants-1980_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04231944