Sodium Iodide → (S)-1-iodo-3-phenyl-3-propanol

HRID 247814

Reaktionsgleichung

Reaktionsgleichung von HRID 247814
Cl[CH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[I-:12].[Na+]>C(N(CC)CC)C.C(C(C)=O)C>[I:12][CH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]

Komponenten

5

Edukt 2

HCID 5238Sodium IodideHCID 2777894(S)-(-)-3-Chloro-1-phenyl-1-propanol

Produkt 1

HCID 14476876(S)-1-iodo-3-phenyl-3-propanolAusbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471TriethylamineKatalysatorHCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

Commerically available (S)-3-chloro-1-phenyl-1-propanol (6 g) was heated with excess sodium iodide (4 equiv., 18 g) and a few drops of triethylamine in 30 mL of methyl ethyl ketone at 100° C. for 20 hours. A sample was taken and monitored by NMR to determine the extent of conversion. The solvent was removed in vacuo and the residue was taken up in dichloromethane and filtered to remove the salts and the iodoalcohol was purified by flash chromatography to yield 6.9 g of product.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. filtrationfiltered
  3. customto remove the salts
  4. customthe iodoalcohol was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-278df93dbd6b44d1b998b0215d6a2550
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208222

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