Silane, (chloromethyl)trimethyl- → HCID 18370002, compound

Participants

Reaction Steps

24.7 ml (20.6 g, 0.17 mol) of chloromethyltrimethylsilane were reacted with 2.92 g (0.42 mol) of lithium powder in 150 ml of pentane (according to the method described in Example 3). The resulting solution of trimethylsilylmethyllithium (about 0.14 mol) in pentane was placed in a 500 ml flask under argon gasification. A solution of 20 g (0.11 mol) of 4,6,6-trimethyl-5,6,7,7a-tetrahydro-1,3-benzodioxol-5-one in 25 ml of tetrahydrofuran was added thereto at −20° C. within about 20 minutes. After a further 20 minutes, the mixture was warmed slowly to room temperature and then cooled to 0° C. Thereafter, 90 ml of water were added dropwise thereto. Subsequently, the water was separated in a water separator and extracted twice with 100 ml of pentane each time. The pentane phases were washed in succession with sodium bicarbonate solution and sodium chloride solution, dried over anhydrous sodium sulphate and concentrated. The crude product (31.9 g) was then crystallized in 60 ml of pentane and cooled to −25° C. The resulting white crystals were filtered off, washed with a small amount of pentane at −20° C. and dried at room temperature under a high vacuum. This gave 30.5 g (almost 100% yield) of 4,6,6-trimethyl-5,6,7,7a-tetrahydro-5-trimethylsilylmethyl-1,3-benzodioxol-5-ol as white crystals, m.p. 63-64.5° C. IR (Nujol, cm−1): 3510 (OH); mass spectrum: 253 (M+—OH, 5), 214 (M—C4H8); 1H-NMR (C6D6, 400 MHz): inter alia 0.27 (s, 9H), 4.9 (s, 1H), 5.19 (s, 1H).

Provenance & Evidence