Ammonium Chloride → (R)-(+)-tert. Butyl 2,6-dimethyl-4-heptenyl ether

A slurry of 2.67 g. (6 mmoles) of isobutyl triphenylphosphonium iodide in 50 ml. of dry tetrahydrofuran was stirred at 0° C. while a solution of 2.94 ml. (6 mmoles) of 2.04 M n-butyllithium in hexane was added dropwise. The resulting mixture was stirred for 10 minutes and then treated with a solution of 0.475 g. (3 mmoles) of (R)-4-tert. butoxy-3-methylbutanal in 25 ml. of dry tetrahydrofuran. After the addition was complete, the reaction mixture was stirred for one hour at room temperature then treated with saturated aqueous NH4Cl and worked up with hexane in the usual manner. The crude product (0.792 g.) was chromatographed on 25 g. of silica gel. Elution with 9:1 parts by volume hexane-ether followed by evaporative distillation gave 0.418 g. (70.4%) of (R)-(+)-tert. butyl-2,6-dimethyl-4-heptenyl ether as a colorless liquid, b.p. 75°-80° C. (bath temperature) (10 mm Hg.); [α]D25 +11.44° (c 0.61, C6H6).

1. additiontreated with a solution of 0.475 g
2. additionAfter the addition
3. stirringthe reaction mixture was stirred for one hour at room temperature
4. customThe crude product (0.792 g.) was chromatographed on 25 g
5. washElution with 9:1 parts by volume hexane-ether
6. distillationfollowed by evaporative distillation
7. customgave 0.418 g

ORD-Eintrag

ord-8c645dbd372b40998f1d58025fdee00e

Quelldatensatz

uspto-grants-1980_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04191842