Sodium hydride → ethyl (RS)-4-(2-methoxycarbonyl-5-benzyloxyphenoxy)-4-phenylbutanoate

HRID 322877

Reaktionsgleichung

Reaktionsgleichung von HRID 322877
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([OH:21])[CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C)C=O>[CH3:18][O:17][C:15]([C:14]1[CH:19]=[CH:20][C:11]([O:10][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:12][C:13]=1[O:21][CH:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:16]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 225489Methyl 4-(benzyloxy)-2-hydroxybenzoateHCID 12847348Ethyl 4-chloro-4-phenylbutanoate

Produkt 1

HCID 23204310ethyl (RS)-4-(2-methoxycarbonyl-5-benzyloxyphenoxy)-4-phenylbutanoateAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred suspension of sodium hydride (340 mg) in dry dimethylformamide (100 mL) is treated portionwise with methyl 4-benzyloxy-2-hydroxybenzoate (2 g). After stirring at ambient temperature for 30 minutes, it is treated with ethyl (RS)-4-chloro-4-phenylbutanoate (1.9 g) in one portion and stirred for 16 hours at ambient temperature, and then for two hours at 80° C. The reaction mixture is then concentrated in vacuo and the residue is partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer is dried over magnesium sulphate, filtered and concentrated in vacuo. Flash chromatography of the resulting oil, eluting with 5-10% ethyl acetate/cyclohexane, affords ethyl (RS)-4-(2-methoxycarbonyl-5-benzyloxyphenoxy)-4-phenylbutanoate (2 g), in the form of a yellow oil.

Aufarbeitung

  1. stirringstirred for 16 hours at ambient temperature
  2. waitfor two hours at 80° C
  3. concentrationThe reaction mixture is then concentrated in vacuo
  4. customthe residue is partitioned between ethyl acetate (100 mL) and water (100 mL)
  5. dry with materialThe organic layer is dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washFlash chromatography of the resulting oil, eluting with 5-10% ethyl acetate/cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-7554c6594e5140b6b1022816babaec49
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211234B1

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