Water → HCID 67119059, compound

A bis(trimethylsilyl)amide lithium-11.0M tetrahydrofuran solution (2.47 ml, 2.47 mmol) was added dropwise to a solution of allyl (4′-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,1′-biphenyl-3-yl)acetate (675 mg, 1.70 mmol) obtained in Example (98-2) in tetrahydrofuran (6 ml) at −78° C. After the mixture was stirred for 30 minutes, methyl iodide (512 μl, 8.22 mmol) was added thereto and the mixture was stirred at −78° C. for 1 hour. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was dissolved in tetrahydrofuran (5 ml). A tetra-n-butylammonium fluoride-1.0M tetrahydrofuran solution (2.04 ml, 2.04 mmol was added to the solution and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane/ethyl acetate=3/1) to give allyl 2-(4′-hydroxy-2-methyl-1,1′-biphenyl-3-yl)propanoate (457 mg, yield: 91%).

1. stirringthe mixture was stirred at −78° C. for 1 hour
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with a saturated aqueous NaCl solution
4. dry with materialdried with anhydrous sodium sulfate
5. customThe residue obtained
6. customby removing the solvent under reduced pressure
7. dissolutionwas dissolved in tetrahydrofuran (5 ml)
8. additionA tetra-n-butylammonium fluoride-1.0M tetrahydrofuran solution (2.04 ml, 2.04 mmol was added to the solution
9. stirringthe mixture was stirred at room temperature overnight
10. additionThe reaction mixture was poured into water
11. extractionextracted with ethyl acetate
12. washThe organic layer was washed with a saturated aqueous NaCl solution
13. dry with materialdried with anhydrous sodium sulfate
14. customThe residue obtained
15. customby removing the solvent under reduced pressure
16. customwas purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane/ethyl acetate=3/1)

ORD record

ord-7cf5c709a23c4d0499ad78e04c1a92b8

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923573B2