Hydrogen Peroxide → HCID 19753535, Verbindung

HRID 2247813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2247813
[CH3:1][O:2][C:3]([CH3:14])(C)[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[CH2:7]1.[CH:15]([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[OH-].[Na+].OO>O1CCCC1>[CH3:1][O:2][CH:3]([CH3:14])[CH2:4][CH:5]([CH3:15])[CH:6]1[CH2:11][CH2:10][CH2:9][CH:8]([OH:12])[CH2:7]1

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 14794002HCID 14794002, Verbindung

Produkt 1

HCID 19753535HCID 19753535, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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 1 M 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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-2d365f77cc864549a176d72d81f545f8
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05037802

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