Trimethyl phosphonoacetate → HCID 69373271, compound

Participants

Reaction Steps

To a solution of 3′-[6-(1-methanesulfonyl-1-methyl-ethyl)quinolin-8-yl]-biphenyl-3-carbaldehyde from Step 1 (1.0 eq.) and (dimethoxy-phosphoryl)-acetic acid methyl ester (1.1 eq.) in THF (0.1M) was added t-BuOK (1.1 eq.; 1.0M in THF). The final mixture was stirred 3 h at rt, poured in saturated aqueous NH4 Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (CH2Cl2:EtOAc; 9:1) afforded the corresponding methyl ester of the title compound as a yellow solid. To a solution of the methyl ester in THF: MeOH (4:1), aqueous NaOH (3.0 eq.) was added. The final mixture was stirred 4 h at rt, neutralized with AcOH, poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound as a white solid.

Provenance & Evidence