Dimethyl Sulfoxide → Benzyl 6-oxohexylcarbamate

HRID 376106

Reaktionsgleichung

Reaktionsgleichung von HRID 376106
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH2:11]([O:18][C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=[O:28])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 4184071Carbamic acid, (6-hydroxyhexyl)-, phenylmethyl ester

Produkt 1

HCID 11391023Benzyl 6-oxohexylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.32 ml (4.40 mmol) of dimethyl sulfoxide is added dropwise under nitrogen to a solution of 0.19 ml (2.20 mmol) of oxalyl chloride in 10 ml of methylene chloride which is being stirred at -50°. The mixture is stirred for 15 minutes, and then 0.5 g (2 mmol) of 6-(N-benzyloxycarbonylamino)hexan-1-ol is added. Stirring is continued at -50° for 25 minutes, 1.78 ml (10 mmol) of N-ethyl-N,N-diisopropylamine are added dropwise and the mixture is poured into 10 ml of ice-water. The organic phase is separated off and the aqueous phase is extracted with 10 ml of methylene chloride. The organic phases are combined, washed twice with 5 ml of N-hydrochloric acid each time and once with 10 ml of saturated sodium chloride solution, dried over magnesium sulfate and concentrated to dryness by evaporation. The resulting oil is purified by chromatography on silica gel with hexane/ethyl acetate (1:1) as eluant. 6-(N-benzyloxycarbonylamino)hexanal is obtained.

Aufarbeitung

  1. stirringThe mixture is stirred for 15 minutes
  2. stirringStirring
  3. customThe organic phase is separated off
  4. extractionthe aqueous phase is extracted with 10 ml of methylene chloride
  5. washwashed twice with 5 ml of N-hydrochloric acid each time
  6. dry with materialonce with 10 ml of saturated sodium chloride solution, dried over magnesium sulfate
  7. concentrationconcentrated to dryness by evaporation
  8. customThe resulting oil is purified by chromatography on silica gel with hexane/ethyl acetate (1:1) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-755e5197606248ab8d01e0d53922ddc1
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05488140

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