Acetic Acid → Ethyl 4-hydroxy-4-(4,5-dimethoxy-2-nitrophenyl)-2-butynoate

1.5 N butyl lithium (26.8 ml, 40.2 mmol) was added to a solution of diisopropylamine (6.0 ml, 42.8 mmol) in tetrahydrofuran (75 ml) under an argon atmosphere at −78° C. The mixture was stirred for one hr. Ethyl propiolate (3.4 ml, 33.5 mmol) and a solution of 4,5-dimethoxy-2-nitrobenzaldehyde (5.0 g, 23.7 mmol) in tetrahydrofuran (50 ml) were added thereto in that order, and the mixture was stirred at −78° C. for additional 1.5 hr. A solution of acetic acid (7.0 ml, 122 mmol) in tetrahydrofuran (20 ml) was added thereto, followed by addition of water. The mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, water, a saturated aqueous sodium hydrogencarbonate solution, and saturated brine solution in that order. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give ethyl 4-hydroxy-4-(4,5-dimethoxy-2-nitrophenyl)-2-butynoate as an oil (8.59 g) The resultant ethyl 4-hydroxy-4-(4,5-dimethoxy-2-nitrophenyl)-2-butynoate was dissolved in toluene (80 ml).

1. stirringin that order, and the mixture was stirred at −78° C. for additional 1.5 hr
2. extractionThe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with dilute hydrochloric acid, water
4. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
5. customThe solvent was evaporated under reduced pressure

ORD record

ord-8911d84290bc446abcca8bfbdd9ea3e6

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07022860B2