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. This was cooled to -75° C. and 63.5 ml. di-isobutylaluminum hydride (1.45 equivalent of hydrogen) was added slowly and allowed to stir for 1 hour. Ethyl acetate (8.8 g., 100 mmol) was added 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 and stirring was continued for 1 hour at 25°-35° C. The material was filtered through Celite twice and evaporated on rotary evaporator at 31° C. in glassware which had been rinsed with 8 N ammonium hydroxide and dried. An inert gas atmosphere must be maintained during all work-up operations. The Z-2-fluoro-3-methyl-4,4-dimethoxy-2-buten-1-al obtained was stored at -20° C. under argon and used as quickly as possible in the next step.

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. waitwas continued for 1 hour at 25°-35° C
6. filtrationThe material was filtered through Celite twice
7. customevaporated on rotary evaporator at 31° C. in glassware which
8. washhad been rinsed with 8 N ammonium hydroxide
9. customdried
10. temperatureAn inert gas atmosphere must be maintained during all work-up operations

ORD record

ord-5f07f45bdfee4d349fc6ddada4582bfe

Source dataset

uspto-grants-1979_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04169100