Acetone Cyanohydrin → 5-[2-(Phenylmethoxy)ethyl]furan-2-propanenitrile

HRID 966900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 966900
CCO[C:4](/[N:6]=N/C(OCC)=O)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O[CH2:33][CH2:34][C:35]1[O:36][C:37]([CH2:40][CH2:41][O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:38][CH:39]=1.CC(C)(O)C#N>C1COCC1>[C:44]1([CH2:43][O:42][CH2:41][CH2:40][C:37]2[O:36][C:35]([CH2:34][CH2:33][C:4]#[N:6])=[CH:39][CH:38]=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Komponenten

6

Edukt 4

HCID 6406Acetone CyanohydrinHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 218751402-(2-Hydroxyethyl)-5-[2-(phenylmethoxy)ethyl]furan

Produkt 1

HCID 218750815-[2-(Phenylmethoxy)ethyl]furan-2-propanenitrileAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

DEAD (1.285 mL, 8.17 mmol) was added to a stirred solution of Ph3P (2.14 g, 8.17 mmol) in 12 mL of dry THF at 0° C. The solution was stirred for 30 min at rt and compound 255E (670 mg, 2.72 mmol) was added. The reaction was stirred for 15 min and acetone cyanohydrin (0.745 mL, 8.17 mmol) was added at −15° C. The reaction was stirred for 30 min at −15° C., then at rt overnight. The mixture was then concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with 100% CH2Cl2 gave 180 mg (0.705 mmol, 26%) of compound 255F as a colorless oil.

Aufarbeitung

  1. stirringThe reaction was stirred for 15 min
  2. stirringThe reaction was stirred for 30 min at −15° C.
  3. customat rt
  4. customovernight
  5. concentrationThe mixture was then concentrated under reduced pressure
  6. customPurification by flash chromatography on silica gel eluting with 100% CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-78b57929cf4f4ba29d4f5f012477dd8a
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06953679B2

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