Diethyl Ether → 1-Cyano-2-[(3-methoxyphenyl)methyl]cyclohexane

HRID 377296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377296
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=O)[CH:12]=[CH:13][CH:14]=1.C1(C)C=CC(S([CH2:32][N+:33]#[C-])(=O)=O)=CC=1.C(OCC)C>C(O)(C)(C)C.COCCOC.COCCOC.O>[C:32]([CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]1[CH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH3:7])[CH:10]=1)#[N:33]

Komponenten

8

Edukt 4

HCID 3283Diethyl EtherHCID 161915Tosylmethyl isocyanideHCID 148680162-(3-Methoxy-benzyl)-cyclohexanoneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 193584921-Cyano-2-[(3-methoxyphenyl)methyl]cyclohexaneAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 86596206tert butanol DMELösungsmittel

Versuchsvorschrift

A solution of potassium tert-butoxide (4.10 g) in tert-butanol-1,2-dimethoxyethane (1:1, 38 ml) was added dropwise to a stirred solution of 2-[(3-methoxyphenyl)-methyl]cyclohexanone (4.10 g) and (p-tolylsulfonyl)methyl isocyanide (4.10 g) in 1,2-dimethoxyethane under ice cooling over 30 minutes. The resulting mixture was stirred at the same temperature for 1 hour and at room temperature for 2 hours and 30 minutes, and then a mixture of diethyl ether and water was added thereto. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was chromatographed over silica gel using n-hexane--ethyl acetate as an eluent to afford 1-cyano-2-[(3-methoxyphenyl)methyl]cyclohexane (3.73 g) as an oil.

Aufarbeitung

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe oily residue was chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8fc6da633c114998b50b57fe3fdebd3a
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025375

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