Lithium Hydroxide → HCID 15480953, compound

To a solution of 1,1'-carbonyldiimiazole (0.20 g, 1.26 mmol) in dichloromethane (10 mL) was added portionwise 3,4-dichlorophenylacetic acid (0.25 g, 1.26 mmol) and the resulting solution stirred under nitrogen for 1 hr, at room temperature. A solution of 8 (0.13 g, 0.5 mmol) in dichloromethane (10 mL) was added and the mixture was allowed to stand at room temperature for 18 hr. The reaction mixture was washed with sodium carbonate solution (2 N, 2×10 mL), dried, and evaporated to give a viscous oil. This material was dissolved in a mixture of tetrahydrofuran (5 mL) and water (5 mL) and treated with lithium hydroxide (42 mg, 1.0 mmol). The reaction mixture was removed, and the aqueous residue was extracted with dichloromethane (3×10 mL). The combined organic extracts were dried and evaporated to give a colorless gum which was purified by flash column chromatography on silica gel, eluting with ethyl acetate-methanol (40:1) to give 9 (155 mg, 70%) as a colorless foam.

1. waitto stand at room temperature for 18 hr
2. washThe reaction mixture was washed with sodium carbonate solution (2 N, 2×10 mL)
3. customdried
4. customevaporated
5. customto give a viscous oil
6. customThe reaction mixture was removed
7. extractionthe aqueous residue was extracted with dichloromethane (3×10 mL)
8. customThe combined organic extracts were dried
9. customevaporated
10. customto give a colorless gum which
11. customwas purified by flash column chromatography on silica gel
12. washeluting with ethyl acetate-methanol (40:1)

ORD record

ord-73607c0afbb54c2390e0022150f9d4ba

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06028063