Hydrochloric Acid → (R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-iodo-cyclopent-2-enone

HRID 1053797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1053797
[I:1]I.N1C=CC=CC=1.[Si:9]([O:16][C@@H:17]1[CH2:21][C:20](=[O:22])[CH:19]=[CH:18]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].Cl>C(Cl)Cl>[Si:9]([O:16][C@@H:17]1[CH2:21][C:20](=[O:22])[C:19]([I:1])=[CH:18]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 1049Pyridine2×HCID 2734530(4R)-(+)-t-Butyldimethylsiloxy-2-cyclopenten-1-one

Produkt 1

HCID 11099812(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-iodo-cyclopent-2-enoneAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

The procedure described in Johnson, C. R., Braun, M. P. J. Am. Chem Soc. 1993, 115, 11014 was followed with modification. A solution of I2 (6.55 g, 25.8 mmol) and pyridine (12 mL) in CH2Cl2 (12 mL) was cannula transferred to a 0° C. solution of (R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone (3.17 g, 14.9 mmol) and pyridine (5.4 mL) in CH2Cl2 (5.4 mL). The reaction was allowed to warm to room temperature and after 2 h, 100 mL 1 M HCl was added. The resulting mixture was extracted with CH2Cl2 (3×60 mL) and the combined organic solution was washed with 100 mL saturated NaHSO3 solution and 50 mL brine and then was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (4.997 g, 99%).

Aufarbeitung

  1. customtransferred to a 0° C.
  2. extractionThe resulting mixture was extracted with CH2Cl2 (3×60 mL)
  3. washthe combined organic solution was washed with 100 mL saturated NaHSO3 solution and 50 mL brine
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash chromatography (ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6d33a35f21de4fbca5d7bce63f42ed93
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394273B2

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