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Hydrochloric Acid → 2-Acetamido-1,3-bis(tert-butyldimethylsilyloxy)-2-(2-(4-(1hydroxy-5-phenylpentyl)phenyl)ethyl)propane

HRID 323804
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 323804
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:13]([NH:16][C:17]([CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([CH:44]=[O:45])=[CH:40][CH:39]=1)([CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])(=[O:15])[CH3:14].Cl>O1CCCC1>[C:13]([NH:16][C:17]([CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([CH:44]([OH:45])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:40][CH:39]=1)([CH2:27][O:28][Si:29]([C:32]([CH3:33])([CH3:34])[CH3:35])([CH3:31])[CH3:30])[CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])(=[O:15])[CH3:14]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 2596681-Bromo-4-phenylbutaneHCID 5462224MagnesiumHCID 155166782-Acetamido-1,3-bis(tert-butyldimethylsilyloxy)-2-(2-(4-formylphenyl)ethyl)propane

Produkt 1

HCID 155166792-Acetamido-1,3-bis(tert-butyldimethylsilyloxy)-2-(2-(4-(1hydroxy-5-phenylpentyl)phenyl)ethyl)propaneAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a solution of magnesium (0.27 g) in anhydrous tetrahydrofuran (5 ml) was dropwise added a solution of 1-bromo-4-phenylbutane (2.35 g) in anhydrous tetrahydrofuran (5 ml) under a nitrogen atmosphere, and the mixture was stirred for 1.5 hours. To this solution was dropwise added a solution of 2-acetamido-1,3-bis(tert-butyldimethylsilyloxy)-2-(2-(4-formylphenyl)ethyl)propane (1.2 g) in anhydrous tetrahydrofuran (15 ml) and the mixture was stirred for 1 hour. 3% Hydrochloric acid was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; hexane: ethyl acetate=2:1) to give the title compound (1.27 g) as a colorless transparent oily substance.

Aufarbeitung

  1. stirringthe mixture was stirred for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent; hexane: ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-ec9877793fb14af1bd41820b95af093c
Quelldatensatz
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06214873B1

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