Bis(acetoxy)iodobenzene → 3-Hydroxy-2,2-dimethyl-5-phenylpentanal

HRID 516655

Reaktionsgleichung

Reaktionsgleichung von HRID 516655
C(OC1C(OC(=O)C)=C(I)C=CC=1)(=O)C.[CH3:16][C:17]([CH3:30])([CH:20]([OH:29])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:18][OH:19].O.C(=O)(O)[O-].[Na+]>ClCCl>[OH:29][CH:20]([CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]([CH3:16])([CH3:30])[CH:18]=[O:19]

Komponenten

5

Edukt 3

HCID 21865429Bis(acetoxy)iodobenzeneHCID 855939482,2-Dimethyl-5-phenyl-1,3-pentanediolHCID 86585896Sodium bicarbonate water

Produkt 1

HCID 157865963-Hydroxy-2,2-dimethyl-5-phenylpentanalAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

DMN-AZADO (2.00 mg, 0.012 mmol) and diacetoxyiodobenzene (117 mg, 0.362 mmol) were added to a dichloromethane solution (0.24 ml) of 2,2-dimethyl-5-phenylpentane-1,3-diol (50.2 mg, 0.241 mmol), and the mixture was stirred at room temperature for 15 min. This was followed by addition of saturated sodium bicarbonate water (1 ml) and a sodium thiosulfate solution (1 ml), and extraction with diethyl ether. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give 3-hydroxy-2,2-dimethyl-5-phenylpentanal (49.2 mg, 92%).

Aufarbeitung

  1. extractiona sodium thiosulfate solution (1 ml), and extraction with diethyl ether
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting residue was then purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b088dd1a3b264c0e82bd6badb58f889f
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09114390B2

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