Benzyl Bromide → Ethyl 2-benzyl-2-cyanoethyl(diethoxymethyl)phosphinate

HRID 5185

Reaktionsgleichung

Reaktionsgleichung von HRID 5185
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([CH2:15][CH2:16][P:17]([CH:22]([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])(=[O:21])[O:18][CH2:19][CH3:20])#[N:14].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH2:29]([CH:15]([C:13]#[N:14])[CH2:16][P:17]([CH:22]([O:23][CH2:24][CH3:25])[O:26][CH2:27][CH3:28])(=[O:21])[O:18][CH2:19][CH3:20])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

8

Edukt 5

HCID 7498Benzyl BromideHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 10037677Ethyl 2-cyanoethyl(diethoxymethyl)phosphinateHCID 178418339Butyllithium

Produkt 1

HCID 14362814Ethyl 2-benzyl-2-cyanoethyl(diethoxymethyl)phosphinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 0.97 g of diisopropylamine in 40 ml of tetrahydrofuran at -78° C. under an atmosphere of nitrogen are added 6.0 ml of a 1.6M solution of n-butyllithium in hexane. This solution is then stirred for a period of 10 minutes at this temperature, after which time a solution of 2.0 g of ethyl 2-cyanoethyl(diethoxymethyl)phosphinate in 10 ml of tetrahydrofuran is added. This mixture is then stirred for a period of 1 hour at -78° C. after which time a solution of 1.4 g of benzyl bromide in 10 ml of tetrahydrofuran is introduced. This mixture is then allowed to warm to room temperature when 40 ml of a saturated ammonium chloride solution is added. The aqueous layer is then extracted with 2×25 ml of diethyl ether and the organic extracts are combined and dried over magnesium sulphate. The solvent is then evaporated under reduced pressure and the crude product chromatographed on silica gel using ethyl acetate as an eluent to give ethyl 2-benzyl-2-cyanoethyl(diethoxymethyl)phosphinate as a viscous oil, 31P=+40.7 and +40.5 ppm (CDCl3).

Aufarbeitung

  1. additionis introduced
  2. additionis added
  3. extractionThe aqueous layer is then extracted with 2×25 ml of diethyl ether
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent is then evaporated under reduced pressure
  6. customthe crude product chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-856eab2a0560410681b793d4b1b773fd
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05243062

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