Pivalic acid → HCID 86744221, compound

Participants

Reaction Conditions

Reaction Steps

Triethyl borane (7.5 ml, 7.5 mmol) was added via syringe to a solution of the β-keto ester (3.17 g, 6.8 mmol, Step F) and pivalic acid (0.069 g, 0.68 mmol) in THF (50 ml) under a dry air atmosphere. The resulting orange solution was cooled to -78° C. and MeOH (10 ml) was added, followed by NaBH4 (0.28 g, 7.5 mmol). The resulting effervescent solution was stirred at -78° C. for five hours. The reaction was quenched by slowly pouring into ice cold H2O2 (5 ml, 30%) and allowing to stir overnight. The reaction was partitioned between H2O and CHCl3. The organics were washed extensively with H2O, dried (MgSO4) and evaporated to give 2.65 g (84%) of a yellow foam which was used in the next step without purification.

Provenance & Evidence