Water → HCID 10749418, compound

Participants

Reaction Steps

Solid NaBH4 (0.19 g, 5.03 mmol) was added portionwise to a stirred solution of 1-methyl-5-nitro-2-pyrrolealdehyde (42) [for preparation see Fournari, P. Bull. Soc. Chim. Fr., 88, 488-491, 1963] (0.78 g, 5.07 mmol) in MeOH (40 mL) at room temperature under N2. After addition was complete, the reaction mixture was stirred for a further 20 min, then water (40 mL) was added and the mixture was saturated with solid K2CO3. Extraction with EtOAc gave 2-hydroxymethyl-1-methyl-5-nitropyrrole (43) (0.77 g, 97%), mp (EtOAc/petroleum ether) 76-77° C. 1H NMR (CDCl3) δ 7.16 (d, J=4.3 Hz, 1 H, H-4), 6.17 (d, J=4.3 Hz, 1 H, H-3), 4.68 (s, 2 H, CH2), 4.02 (s, 3 H, CH3). Anal. Calculated for C6H8N2O3 : C, 45.1; H, 5.2; N, 17.9. Found: C, 46.1; H, 5.1; N, 17.6%.

Provenance & Evidence