Diisobutylaluminum hydride → 5-Bromo-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-Bromo-3,3-dimethyl-3H-benzofuran-2-one (1.199 g, 5.0 mmol) (described in Step 2 of Example A(68), ), dissolved in anhydrous CH2Cl2 (20 ml), and cooled to −78° C., was added DIBAL (3.67 mL, 5.5 mmol, 1.5M in Toluene). The reaction was stirred for 1 h at this temperature then quenched with 1N HCl until acidic. The resulting mixture was extracted with ether, which was washed with brine, dried with MgSO4, concentrated and purified by silica gel chromatography (gradient elution 5–15% Ethylacetate/Hexanes). Yield 0.95 g, 79%.

Provenance & Evidence