2h 5 02 s 2h 6 70 s 1h 6 77 dd 1h 7 19 d 1h 7 30 m 1h 7 37 t 2h 7 42 d 2h ir kbr u03bdmax 3460 s 3100 m 3260 m 2950 s 2900 s 1610 s 1590 m 1515 s rf 0 22 hexane ethyl acetate 2 1 2 3 benzyloxy 1 3 5 10 estratriene 1 methyl 17 u03b2 oxy ethanol ii 2 m p 103 5 u00b0 104 5 u00b0 c 2 31 g produced according to the process of example 3 and dichloromethane 15 ml were placed and dissolved in an eggplant type flask 100 ml to this solution were added dihydropyran 924 mg and pyridinium p toluenesulfonate ppts 138 mg and the mixture was stirred overnight at room temperature the reaction solution was distilled and the residue was dissolved in ethyl acetate 50 ml washed twice with water 15 ml and further washed with a saturated saline solution 15 ml the washings were dried over na 2 so 4 filtered and distilled to form an oily substance 3 19 g this substance was purified by silica gel chromatography hexane ethyl acetate 5 1 to give a purified product 2 42 g the progress of the reaction was confirmed by tlc check the purified product was dissolved in dioxane 238 ml and 10 pd c was added to the solution this solution was treated with h 2 gas at room temperature for 5 hours to obtain a debenzylated compound 1 77 g this compound was dissolved in dry dichloromethane 30 ml followed by addition of pyridine 8 5 ml and benzoyl chloride 596 0 ml.