1-(Chloromethyl)-4-iodobenzene → Ethyl 18-(p-iodophenyl)octadecanoate

HRID 1367726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1367726
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[I:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1>CC(N(C)C)=O.[Zn].C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni].IC1C=CC(CCCCCCCCCCCCCCCCCCO)=CC=1>[I:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:26][CH:25]=1

Komponenten

7

Edukt 2

HCID 8172111-(Chloromethyl)-4-iodobenzeneHCID 86625642Ethyl 17-iodoheptadecanoate

Produkt 1

HCID 57548711Ethyl 18-(p-iodophenyl)octadecanoateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23994ZincKatalysatorHCID 6433264Bis(1,5-cyclooctadiene)nickelKatalysatorHCID 1165580418-(p-Iodophenyl)octadecanolKatalysatorHCID 31374DimethylacetamideLösungsmittel3×

Versuchsvorschrift

Zinc powder (70 mg, 1.06 mmol) was dried at 70° C. for 30 min in a sealed tube, then DMA (0.4 ml) and solid 12 (9 mg, 0.04 mmol) were added. After stirring for 10 min, a solution of ethyl 17-iodo-heptadecanoate 80 (300 mg, 0.71 mmol) in DMA (1.5 ml) was added and the reaction mixture was stirred in the sealed tube for 11 h at 70° C. In a 10-ml flask, Ni(COD)2 (10 mg, 0.04 mmol), (R)-(s-Bu)-Pybox (or (S)-(s-Bu)-Pybox) (23 mg, 0.07 mmol) and p-iodobenzyl chloride 82 (252 mg, 1 mmol) were dissolved in DMA (1.5 ml), then organozinc solution 81 was added via cannula. The mixture was stirred at room temperature for 15 h, and the reaction was quenched by addition of aqueous NH4Cl, extracted with EtOAc, the extract was dried over Na2SO4 and evaporated. Chromatography of the crude product in hexane-ether (97:3) yielded the compound 37 (276 mg, 76%).

Aufarbeitung

  1. stirringthe reaction mixture was stirred in the sealed tube for 11 h at 70° C
  2. stirringThe mixture was stirred at room temperature for 15 h
  3. customthe reaction was quenched by addition of aqueous NH4Cl
  4. extractionextracted with EtOAc
  5. dry with materialthe extract was dried over Na2SO4
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c3c51c7e1e64448e9c1e26e6e91eb2b3
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893286B2

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