Water → HCID 18552227, compound

Participants

Reaction Conditions

Reaction Steps

Ammonium chloride (152.9 g, 2.858 mol), 1 (225.0 g, 0.572 mol), water (2.8 L), methanol (3.8 L) were combined and mechanically stirred at 50° C., then powdered iron (95.9 g, 1.715 mol) was added portionwise over ten minutes. The suspension was vigorously stirred at reflux for 2.5 hours, then hot filtered through a celite pad. The pad was rinsed with water (3×700 mL) and CH2Cl2 (5×700 mL). The aqueous layer was extracted with CH2Cl2 (3×1 L), then concentrated to remove methanol and again extracted with CH2Cl2 (3×500 ml). The combined organics were washed with water (2×3 L), dried (Na2SO4), filtered, and spin-evaporated to give 198.1 g (95.3% yield) of 2 as a pale yellow solid. TLC (7:1 hexanes/EtOAc) indicated a single spot. This lot was combined with that of a 100 mmol run to give a total of 231 g of 2 (94.3% yield) which was suitable for further transformation.

Provenance & Evidence