Sodium bis(2-methoxyethoxy)aluminiumhydride → 6-Bromospiro[indoline-3,3'-thietane]

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromospiro[indoline-3,3′-thietan]-2-one (0.260 g, 0.962 mmol) in toluene (39 mL) was added sodium bis(2-methoxyethoxy)aluminium hydride (60% in toluene, 1.47 mL, 4.81 mmol) dropwise under an atmosphere of argon gas. The solution was stirred at 80° C. for 40 min, cooled in an ice bath, quenched with aqueous 2N NaOH and treated with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated in vacuo to give 6-bromo-1,2-dihydrospiro[indole-3,3′-thietane] as a tan solid. Mass Spectrum (ESI) m/e=256.0 [(M+1) (79Br)] and 258.0 [(M+1) (81Br)].

Provenance & Evidence