Acetic Acid → HCID 15029690, compound

Sodium hydride (content:62%, 3.3 g) was suspended in tetrahydrofuran (30 ml). The suspension was ice-cooled in an atmosphere of argon gas. A solution of t-butyl diethylphosphonoacetate (20.9 g) in tetrahydrofuran (20 ml) was added to the suspension. The mixture was stirred for 15 min. at room temperature. A solution of 2-hydroxy-5-nitrobenzaldehyde (6.6 g) in tetrahydrofuran (20 ml) was gradually added to the mixture often with ice-cooling. The mixture was stirred for 10 min. at room temperature. Acetic acid was gradually added to the mixture until pH of the mixture was down to 5.0. The reaction mixture was gel-filtered with using YMC gel. Moreover the gel was washed with ethyl acetate. A mixture of the filtrate and washings was evaporated. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1→3:2) to give the title compound (10.0 g) having the following physical data.

1. temperaturecooled in an atmosphere of argon gas
2. temperaturecooling
3. stirringThe mixture was stirred for 10 min. at room temperature
4. filtrationThe reaction mixture was gel-filtered with using YMC gel
5. washMoreover the gel was washed with ethyl acetate
6. additionA mixture of the filtrate and washings
7. customwas evaporated
8. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1→3:2)

ORD record

ord-afa7f6a66470472aa3af0c800e5b7793

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06001877