Water → HCID 86701857, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-oxo-3,3a,4,8b-tetrahydroindeno[1,2-b]pyrrole-1-carboxylate (200 mg, 0.81 mmol) was dissolved in tetrahydrofuran (8 mL) was cooled to −78° C. Then, lithium bis(trimethylsilyl)amide (1 mol/L in THF, 1.22 mL, 1.22 mmol) was added. After 1 h at −78° C., ethyl formate (0.198 mL, 2.446 mmol) was added. The mixture was stirred for another 30 min and then allowed to warm to room temperature. After another 30 min, water was added. The mixture was extracted with diethylether, the pH of the aqueous layer was adjusted to 1 and the solution was extracted with EtOAc (2*20 mL), dried (Na2SO4) and concentrated to give a colourless oil ethyl (3E)-3-(hydroxymethylene)-2-oxo-4,8b-dihydro-3aH-indeno[1,2-b]pyrrole-1-carboxylate D12 (120 mg, 54%) which was used without further purification in the next step. LCMS (Method A): RT: 1.53 min; ES− 272 [M−H]

Provenance & Evidence