Hydrogen Peroxide → HCID 19753535, Verbindung

3-(3-methoxy-3-methylbut-1-yl)cyclohexanone (1.4 g. 0.0051 mol) was dissolved in tetrahydrofuran (10 mL) and cooled to -78~C. under a nitrogen atmosphere with stirring. A solution of lithium tri-sec-butylborohydride (6.1 mL of a 1M solution of tetrahydrofuran, 0.0061 mol) was added. The mixture was allowed to come to 20~C. over 16 hours and 10% NaOH (aq, 4.0 mL) was added, followed by 30% hydrogen peroxide (aq, 4.0 mL). The mixture was extracted with hexane. The extracts were dried (Na2SO4) and concentrated to the residue which was purified by bulb to bulb distillation (air bath temp 175~C., 0.1 mm Hg) to yield 3-(3-methoxy-methylbut-1-yl)cyclohexanol as a mixture of diastereoisomers in the ratio of 94:6 (0.7 g). NMR(CDCl3)δ 1.1(s,6H), 1.2-1.8(m,13H), 3.2(s,3H), 4.1(brs,1H). IR (neat) 3410, 2990, 2960, 2870, 1460, 1370, 1110, 1090, 980 cm-1. MS (m/e) 43, 73, 109, 124, 143, 181, 201, 214.

1. temperaturecooled to -78~C
2. extractionThe mixture was extracted with hexane
3. dry with materialThe extracts were dried (Na2SO4)
4. concentrationconcentrated to the residue which
5. distillationwas purified by bulb to bulb distillation (air bath temp 175~C., 0.1 mm Hg)

ORD-Eintrag

ord-75c8f79c31e84c02ba41d4431360acc2

Quelldatensatz

uspto-grants-1993_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05225608