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The title compound was obtained from 2-hydroxy-5-methoxy-benzaldehyde using the method described in Chem Pharm Bull 27 (6), 1979, pp 1490-1494: Ethyl chloroformate (571 muL, 6.0 mmol) was added dropwise over a period of 30 minutes to an ice cold solution of 2-hydroxy-5- methoxy-benzaldehyde (624 muL, 5.0 mmol) and triethyl amine (832 muL, 6.0 mmol) in THF (5 mL) and the mixture was stirred at 0C for 30 more minutes. The precipitate was filtered off and the filtrate was dropwise over a period of 45 minutes added to an ice cold solution OfNaBH4 (756 mg, 20 mmol) in water (7.5 mL). The resulting mixture was stirred at room temperature for 90 minutes, then diluted with water, acidified to pH < 2 with 2 M HCl and extracted with ether. The organic phase was dried (MgSO4) and evaporated. When 90 % of the ether had evaporated a precipitate formed that was filtered away. The title compound was in the filtrate. Quantitative yield.
(4aS,4bR,6aS,12aS,12bR,14aS)-10-Methoxy-1,1,4a,6a,8,12b-hexamethyl-2,3,4,4a,4b,5,6,6a,12,12a,12b,13,14,14a-tetradecahydro-1H-7-oxa-benzo[b]chrysene[ No CAS ]
from 2-hydroxy-5-methoxy-toluene and bromobenzene there is obtained 5-methoxy-2-phenoxy-toluene of boiling point 102-104 C./0.035 Torr and melting point 39-42 C. and therefrom by methyl ether cleavage there is obtained p-phenoxy-m-cresol, m.p. 96-99 C.
With tellurium tetrachloride; In dichloromethane; at 20℃; for 0.05h;Inert atmosphere;
General procedure: To a 50 mL round bottomed flask containing a solution of 1 (272 mg, 1.0 mmol) and appropriate alcohol (1.2 mmol) in dichloromethane (10 mL) at 0 C under argon was added TeCl4 (5 mg, 2 mol %). The ice bath was removed and the mixture was stirred for the time indicated in Tables 2 and 6. A saturated solution of ammonium chloride (5 mL) was then added and the mixture was extracted with EtOAc (2×10 mL). The combined organic phases were dried over MgSO4 and the solvents were removed under reduced pressure followed by purification by a flash column chromatography [hexanes/EtOAc (95:5)] to yield the corresponding 2,3-unsaturated O-glycopyranosides.
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