Trimethyl phosphonoacetate → HCID 69858985, Verbindung

Temperatur

-78 °C

To a solution of trimethyl phosphonoacetate (412 mg, 2.26 mmol) in THF (15 mL) at 0° C. was added 1M sodium bis(trimethylsilyl)amide in THF (2.26 mL, 2.26 mmol) dropwise. After stirring 15 min the mixture was cooled to −78° C. and a solution of aldehyde (4) (625 mg, 1.89 mmol) in THF (8 mL) was added dropwise. The solution was allowed to warm to rt. After stirring 4 h, brine was added and the mixture was extracted with EtOAc. The combined organic layers were washed with water, brine, and dried (MgSO4). The solvent was removed under reduced pressure and the residue was chromatographed (silica gel, 7.5 to 15% EtOAc/hexanes) to give the ester (5) as a white solid (658 mg, 90%): 1 H NMR (CDCl3) δ 7.52 (d, J=16.1 Hz, 1 H), 7.15 (m, 11 H), 6.86 (d, J=8.1 Hz, 2 H), 6.28 (d, J=16.1 Hz, 1 H), 3.76 (s, 3 H), 2.47 (q, J=7.7 Hz, 2 H), 0.93 (t, J=7.7 Hz, 3 H); APcI m/z: 428 (M+H+CH3CN+, 100%).

1. temperatureto warm to rt
2. stirringAfter stirring 4 h
3. extractionthe mixture was extracted with EtOAc
4. washThe combined organic layers were washed with water, brine
5. dry with materialdried (MgSO4)
6. customThe solvent was removed under reduced pressure
7. customthe residue was chromatographed (silica gel, 7.5 to 15% EtOAc/hexanes)

ORD-Eintrag

ord-9886edc9a2ef4d41a662626952c86ab6

Quelldatensatz

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06528681B2