tert-Butyl hydroperoxide → (2S,3S)-3-heptyloxiranemethanol

HRID 1199504

Reaktionsgleichung

Reaktionsgleichung von HRID 1199504
C([O:5]O)(C)(C)C.[CH2:7]([OH:17])/[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>ClCCl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH2:10]([C@@H:9]1[O:5][C@H:8]1[CH2:7][OH:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

5

Edukt 2

HCID 6410tert-Butyl hydroperoxideHCID 53649422-Decenol, (2E)-

Produkt 1

HCID 11019334(2S,3S)-3-heptyloxiranemethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026Titanium isopropoxideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A flame-dried 100 mL round bottom 3-necked (RB3N) flask (note 1) filled with thermometer, stopcock, septum, and stirbar was purged with argon, charged with 4 A molecular sieves (300 mg; note 2) and 30 mL of dichloromethane (note 3), and cooled to -22° (30% ethylene glycol/water/dry ice). R,R-(+)-diethyl tartrate (97 mg; 47 mmol; note 4) and titanium(IV)isopropoxide (91 mg; 0.32 mmol; note 5) were added, and the mixture was stirred at -22±2° for 10 min. t-Butyl hydroperoxide (2.2 mL of a 5.8M dichloromethane solution; note 6) was added, and the mixture was stirred at -22±2° for 30 min. A solution of trans-2-decen-1-ol (1.00 g; 6.4 mmol; note 7) in dichloromethane, was then added. The mixture was stirred under argon at -22±2° until analysis (note 8) indicated >95% reaction (2.5 hr).

Aufarbeitung

  1. additionA flame-dried 100 mL round bottom 3-necked (RB3N) flask (note 1) filled with thermometer, stopcock, septum, and stirbar
  2. customwas purged with argon
  3. additioncharged with 4 A molecular sieves (300 mg; note 2) and 30 mL of dichloromethane (note 3)
  4. temperaturecooled to -22° (30% ethylene glycol/water/dry ice)
  5. additionnote 6) was added
  6. stirringThe mixture was stirred under argon at -22±2° until analysis (note 8)
  7. custom>95% reaction (2.5 hr)

Quellen und Nachweise

ORD-Eintrag
ord-9b48e687ff454932803f8f04f2b1e208
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04900847

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