4-Methoxybenzyl alcohol → HCID 86732774, compound

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Reaction Steps

To a solution of (R)-2,5-dioxotetrahydrofuran-3-yl 2,2,2-trifluoroacetate (85 g, 401 mmol) in Dichloromethane (DCM) (600 mL) was added (4-methoxyphenyl)methanol (150 mL, 1202 mmol). The mixture was stirred at rt for 3 h and then extracted three times with 10% aqueous solution of NaHCO3. The combined aqueous extracts were washed with DCM, acidified to pH 2 with 2 N HCl, and then extracted with DCM. The organic layer was dried over sodium sulfate and filtered. To the filtrate was added (E)-tert-butyl N,N′-diisopropylcarbamimidate (161 g, 802 mmol) dropwise over 1 h. The mixture was stirred at rt overnight. The precipitate was removed by filtration and the filtrate was purified by normal phase automatic silica column chromatography (Combiflash RF), eluting with EA/Hexane (10-80%) to afford (R)-4-tert-butyl 1-(4-methoxybenzyl) 2-hydroxysuccinate (62.5 g, 201 mmol, 50.2% yield) as a colorless oil. LCMS: (M+Na)+: 333.1

Provenance & Evidence