Diethyl Sulfate → Ethyl 2-ethoxy-3-(3-nitrophenyl)prop-2-enoate

Diethyl sulfate (12 g, 78.2 mmol) was added to a stirred mixture of 2-hydroxy-3-(3-nitrophenyl)acrylic acid (6.1 g, 30.0 mmol) and caesium carbonate (29.3 g, 90 mmol) in DMF (61 ml) to form a dear, pale yellow mixture, which was stirred at RT overnight. The resulting dark red suspension was heated to 50° C. for 4 h then concentrated in vacuo and the residue partitioned between water (100 ml) and dichloromethane (150 ml). The organic layer was separated, further washed with water (2×100 ml), dried over sodium sulphate and filtered through a silica gel pad. The resulting yellow solution was evaporated to dryness in vacuo to give ethyl 2-ethoxy-3-(3-nitrophenyl)acrylate as a yellow solid (5.6 g, 72%).

1. customto form a dear, pale yellow mixture, which
2. temperatureThe resulting dark red suspension was heated to 50° C. for 4 h
3. concentrationthen concentrated in vacuo
4. customthe residue partitioned between water (100 ml) and dichloromethane (150 ml)
5. customThe organic layer was separated
6. washfurther washed with water (2×100 ml)
7. dry with materialdried over sodium sulphate
8. filtrationfiltered through a silica gel pad
9. customThe resulting yellow solution was evaporated to dryness in vacuo

ORD record

ord-1d0c52fad3824ece962dc336d9819fdc

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133099B2