Hydrochloric Acid → Tridec-12-en-1-ol

This example illustrates the synthesis of 1-(12-Tridecenyl)-3,7-dimethylxanthine (CT2555). To a suspension of magnesium (4.12 g, 172 mmol) and a crystal of iodine in tetrahydrofuran (40 ml) was added 10-undecenyl bromide (8.00 g, 34.3 mmol) in tetrahydrofuran (30 ml) over 30 min and the reaction stirred for a further 30 min after the addition was complete. The solution was added via a canula over 5 min to a solution of ethylene oxide (2.65 g, 60.0 mmol) in tetrahydrofuran (30 ml) and stirred at 25° C. for 16 hr. Saturated ammonium chloride (100 ml) and 1M hydrogen chloride (200 ml) were added and extracted with diethyl ether (2×200 ml). The combined organic extracts were dried (magnesium sulfate) and evaporated to give a residue which was distilled at 1.5 mm Hg to afford 12-tridecenyl alcohol as a clear liquid (4.11 g, 61%, b.p. 98°- 101° C.).

1. additionafter the addition
2. stirringstirred at 25° C. for 16 hr
3. extractionextracted with diethyl ether (2×200 ml)
4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
5. customevaporated
6. customto give a residue which
7. distillationwas distilled at 1.5 mm Hg

ORD record

ord-11ab1ced4213430a9db31e741ab7d06b

Source dataset

uspto-grants-1996_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05521315