Diisobutylaluminum hydride → 3-Benzofuranol, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2,3-dihydro-

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Reaction Conditions

Reaction Steps

To a stirred solution of 6-tert-Butyldimethylsilyloxy-2,3-dihydrobenzofuran-3-one (42 g, 158 mmol) in dichloromethane (1.4 L) at −78° C. under nitrogen was slowly added a solution of DIBAL-H (238 mL, 1.0 M, 238 mmol) in dichloromethane. The reaction was stirred at −78° C. for 1 h, and then was quenched carefully with ethyl acetate (1.0 L). Cold bath was removed, and a solution of Rochelle's salt (400 mL, 10%) was added continuously with stirring over a period of 2 h. The mixture was then diluted with MTBE (4.0 L), washed with brine, dried with magnesium sulfate, filtered and concentrated to yield the final product as yellow oil.

Provenance & Evidence