HCID 56998111, compound → HCID 68538468, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[3-(3-ethoxy-3-oxopropyl)phenyl]propanoic acid (10.7 g) and TEA (6.28 mL) in THF (100 mL) was added isobutyl chloroforamate (5.82 mL) dropwise at 0° C. The reaction mixture was stirred at the same temperature for 5 minutes and filtered. And the precipitate was and rinsed with THF (50 mL). The filtrate and the rinse liquid were combined and the resultant mixture was cooled at 0° C. To the resultant mixture was added sodium borohydride (2.43 g) followed by adding water (1.21 mL) dropwise at the same temperature. The reaction mixture was quenched and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=7:3) to afford ethyl 3-[3-(3-hydroxypropyl)phenyl]propanoate (5.60 g) a colorless oil.

Provenance & Evidence