Hydrochloric Acid → HCID 67119355, compound

A sec-butyl lithium-1.00M cyclohexane-n-hexane mixture solution (29.8 ml, 29.8 mmol) was added dropwise to a solution of 1-tert-butyl-3-(dimethoxymethyl)-2-(methoxymethoxy)benzene (4.00 g, 14.9 mmol) obtained in Example (10-1) and N,N,N′,N′-tetramethylethylenediamine (4.72 ml, 31.3 mmol) in diethyl ether (100 ml) at −40° C. over 20 minutes. After the reaction mixture was stirred at room temperature for 1 hour, it was cooled to −20° C. and N,N-dimethylformamide (2.30 ml, 31.3 mmol) was added thereto. After the temperature of the reaction mixture was returned to room temperature and the mixture was further stirred for 1 hour, the mixture was carefully poured into cold 0.1N hydrochloric acid and the mixture was extracted with ethyl acetate (three times). The combined organic layer was successively washed with 0.1N hydrochloric acid, water (three times) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a residue. The obtained residue was dissolved in methanol (10 ml) and sodium borohydride (111 mg, 3.00 mmol) was added thereto under ice-cooling, and the mixture was stirred at room temperature overnight. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate (four times), the organic layer was successively washed with water (twice) and 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 column chromatography (eluting solvent: n-hexane/ethyl acetate=10/1-3/1) to give [4-tert-butyl-2-(dimethoxymethyl)-3-(methoxymethoxy)phenyl]methanol (350 mg, yield: 8%).

1. temperatureit was cooled to −20° C.
2. customwas returned to room temperature
3. stirringthe mixture was further stirred for 1 hour
4. extractionthe mixture was extracted with ethyl acetate (three times)
5. washThe combined organic layer was successively washed with 0.1N hydrochloric acid, water (three times)
6. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
7. customThe solvent was removed under reduced pressure
8. customto give a residue
9. temperatureunder ice-cooling
10. stirringthe mixture was stirred at room temperature overnight
11. extractionthe mixture was extracted with ethyl acetate (four times)
12. washthe organic layer was successively washed with water (twice) and 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 column chromatography (eluting solvent: n-hexane/ethyl acetate=10/1-3/1)

ORD record

ord-1959fb2193b947aba58bed2da97862a0

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923573B2