Methanol → 4-(2,3-Dihydroxypropyl)-3-methoxybenzonitrile

HRID 1519594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519594
[CH2:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[O:12][CH3:13])C=C.C[N+]1([O-])CC[O:18][CH2:17]C1.[CH3:22][OH:23]>O.O=[Os](=O)(=O)=O>[OH:23][CH:22]([CH2:17][OH:18])[CH2:1][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[O:12][CH3:13]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 82029Methyl morpholine oxideHCID 675133484-Allyl-3-methoxybenzonitrile

Produkt 1

HCID 675137884-(2,3-Dihydroxypropyl)-3-methoxybenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 4-allyl-3-methoxybenzonitrile (1.1 g, 6.4 mmol) in 30 mL of methanol and 10 mL of water was added OsO4 (140 mg) and NMO (2.2 g, 16 mmol), and the mixture was stirred at ambient temperature overnight. Remove the methanol under reduced pressure, the residue was dissolved in EtOAc, washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by fast column chromatograph to give 4-(2,3-dihydroxypropyl)-3-methoxybenzonitrile. MS m/z: 208 (M+1)+.

Aufarbeitung

  1. customRemove the methanol under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by fast column chromatograph

Quellen und Nachweise

ORD-Eintrag
ord-edd16adcc06449d692b2aab77a693426
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073882B2

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