tert-Butyl methyl ether → 4-(cis-3-Allylcyclohexyloxymethyl)-2-(3-methoxyphenyl)-5-methyloxazole

HRID 854665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854665
[CH2:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([OH:10])[CH2:5]1)[CH:2]=[CH2:3].[H-].[Na+].I[CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)[O:18][C:19]=1[CH3:20].C(OC)(C)(C)C>CN(C)C=O>[CH2:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([O:10][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)[O:18][C:19]=2[CH3:20])[CH2:5]1)[CH:2]=[CH2:3]

Komponenten

6

Edukt 4

HCID 15413tert-Butyl methyl etherHCID 24758Sodium hydrideHCID 219803164-Iodomethyl-2-(3-methoxyphenyl)-5-methyloxazoleHCID 58763359cis-3-Allylcyclohexanol

Produkt 1

HCID 692437494-(cis-3-Allylcyclohexyloxymethyl)-2-(3-methoxyphenyl)-5-methyloxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

1.8 g of cis-3-allylcyclohexanol are dissolved in 20 ml of dimethyl-formamide, and 770 mg of sodium hydride (60% strength suspension in paraffin oil) are added. After 30 minutes, 4 g of 4-iodomethyl-5-methyl-2-(3-methoxyphenyl)oxazole, dissolved in 20 ml of dimethylformamide, are added dropwise. The mixture is stirred at room temperature for 1 hour. 200 ml of methyl tert-butyl ether are then added to the reaction mixture, and the mixture is washed three times with water. The organic phase is dried over MgSO4 and the solvent is then removed under reduced pressure. The residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate=10:1. This gives 750 mg of 4-(cis-3-allyl-cyclohexyloxymethyl)-2-(3-meLhoxpheny,”-5-methyloxazole as an Oil. C21H27NO3 (341.45), MS(ESI): 342 (M+H+), Rf(n-heptane:ethyl acetate=2:1)=0.26.

Aufarbeitung

  1. additionare added dropwise
  2. washthe mixture is washed three times with water
  3. dry with materialThe organic phase is dried over MgSO4
  4. customthe solvent is then removed under reduced pressure
  5. customThe residue is purified on silica gel using the mobile phase n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-89036446ff29479cb7671895721c091f
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259177B2

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