Tetrahydrofuran → HCID 15409727, compound

Participants

Reaction Steps

The solution of trimethylsilylmethyllithium (about 0.43 mol) prepared from 8.7 g (1.25 mol) of lithium powder and 74 ml (61.6 g, 0.5 mol) of chloromethyltrimethylsilane in 450 ml of pentane was placed in a 750 ml four-necked sulphonation flask provided with a magnetic stirrer, dropping funnel, condenser and argon gasification. Then a solution of 60.0 g (0.33 mol) of 4,6,6-trimethyl-5,6,7,7a-tetrahydro-1,3-benzodioxol-5-one in 75 ml of tetrahydrofuran was added dropwise thereto at −20° C. within 30 minutes. The mixture was warmed slowly to room temperature and subsequently the pentane was distilled off up to the boiling point 62° C. over a Vigreux column. The pentane, which was distilled off, was replaced continuously with 500 ml of tetrahydrofuran. Finally, the mixture was heated at reflux for 12 hours under GC control. Subsequently, it was cooled to 0° C., 200 ml of water were added dropwise, the phases were separated and the aqueous phase was extracted three times with 100 ml of pentane each time. The entire organic phase was washed with 150 ml of saturated sodium bicarbonate solution and sodium chloride solution, dried over anhydrous sodium sulphate, filtered and concentrated. This gave 67.5 g of a yellow oil, which was distilled over a 10 cm packed column. At a boiling temperature of 38° C./0.04 mbar (4 Pa) there were obtained 49.0 g (82% yield) of 4,6,6-trimethyl-5,6,7,7a-tetrahydro-5-methylidene-1,3-benzodioxol as a colorless oil. The analytical data of the product were the same as those of the product of Example 7.

Provenance & Evidence