HCID 56998111, compound → HCID 68538468, compound

Temperature

0 °C

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.

1. filtrationfiltered
2. washrinsed with THF (50 mL)
3. additionTo the resultant mixture was added sodium borohydride (2.43 g)
4. additionby adding water (1.21 mL) dropwise at the same temperature
5. customThe reaction mixture was quenched
6. extractionextracted with EtOAc
7. washThe organic layer was washed with brine
8. dry with materialdried over anhydrous MgSO4
9. filtrationfiltered
10. customevaporated in vacuo
11. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=7:3)

ORD record

ord-1af41a53a9894bdc9ef2f5693e6fc6cd

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273745B2