tert-Butyldimethylsilyl chloride → HCID 86678084, compound

Participants

Reaction Steps

The alcohol (11Z,14Z)-methyl 3-hydroxyicosa-11,14-dienoate (3) (1.40 g, 4.14 mmol) in pyridine:THF (2:1, 30 mL) was treated with silver nitrate (913 mg, 5.40 mmol), t-butylchlorodimethyl silane (814 mg, 5.40 mmol) and stirred (60 min) The mixture was filtered through Celite and the filter cake rinsed with pyridine. The filtrate was concentrated and the residue was taken-up in CH2Cl2, washed with HCl (5%, aq.) and brine, dried, filtered and concentrated. The crude material was subjected to chromatography to yield (11Z,14Z)-methyl 3-((tert-butyldimethylsilyl)oxy)icosa-11,14-dienoate (4) (1.70 g, 91%) as a clear colorless oil. Rf 0.8 (10% EtOAc-hexanes), FW 452.79, C27H52O3Si.

Provenance & Evidence