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

HRID 2110427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110427
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-e1c682263a224a38bd5c2b85644f312e
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517904B2

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