Triethylamine → Dihydrosafrole

Homopiperonyl alcohol (1) (7.03g, 42.4 mmol)1,2,3 and triethylamine (8.59 g., 85.0 mmol) were dissolved in methylene chloride (100 ml). The mixture was cooled to 0°-5°, then methanesulfonyl chloride (7.31 g., 63.6 mmol) was added slowly dropwise to the vigorously stirred solution. The mixture was stirred an additional 30 mins., then transferred to a separatory funnel where it was washed with water (3 × 50 ml), 4% hydrochloric acid (3 × 50 ml), saturated sodium bicarbonate solution (25 ml), saturated brine (25 ml) and dried over sodium sulfate. Filtration and evaporation of the methylene chloride yielded 9.76 g of a brown oil (94%); NMR--(CDCl3) 6.72 (m, 3H), 5.92 (S, 2H), 4.34 (t, J=7, 2H), 2.95 (t, J=7), lying under 2.89 (s) giving a total integration of 5H. This material was used without further purification.

1. temperatureThe mixture was cooled to 0°-5°
2. custom, then transferred to a separatory funnel
3. washwhere it was washed with water (3 × 50 ml), 4% hydrochloric acid (3 × 50 ml), saturated sodium bicarbonate solution (25 ml), saturated brine (25 ml)
4. dry with materialdried over sodium sulfate
5. filtrationFiltration and evaporation of the methylene chloride

ORDレコード

ord-32d23eaea49446be9e9ad320385f767c

出典データセット

uspto-grants-1977_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04059593