Formaldehyde → HCID 86723957, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (2.7 g, 10.1 mmol), potassium carbonate (4.2 g, 30.3 mmol), THF (150 mL) and paraformaldehyde (7.2 g, 0.24 mol) was stirred at 20° C. for 2 h then was poured onto ice (100 g) and saturated aqueous NaHCO3 (100 mL) and extracted with EtOAc (4×100 mL). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo. Chromatography (SiO2; gradient elution with 30-100% EtOAc in petrol) gave an orange solid (3.7 g). Crystallisation from EtOAc and petrol gave the title compound (1.23 g). Chromatography of the mother liquor gave further product (0.978 g). MS: [M-tert-Bu]+=272 (fragment ion).

Provenance & Evidence