Chlorotrimethylsilane → HCID 59633933, Verbindung

HRID 1615052Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1615052
[Cl-].[Li+].BrC(Br)C.Cl[Si](C)(C)C.[C:12]([N:19]1[CH2:22][CH:21](I)[CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[CH:24]1([C:27]2[CH:43]=[CH:42][C:30]([CH2:31][O:32][C:33]3[CH:38]=[CH:37][C:36](I)=[CH:35][C:34]=3[O:40][CH3:41])=[CH:29][CH:28]=2)[CH2:26][CH2:25]1>O1CCCC1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Zn]>[CH:24]1([C:27]2[CH:43]=[CH:42][C:30]([CH2:31][O:32][C:33]3[CH:38]=[CH:37][C:36]([CH:21]4[CH2:22][N:19]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:20]4)=[CH:35][C:34]=3[O:40][CH3:41])=[CH:29][CH:28]=2)[CH2:25][CH2:26]1

Komponenten

9

Edukt 5

HCID 6397ChlorotrimethylsilaneHCID 112011,1-DibromoethaneHCID 433294Lithium ChlorideHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylateHCID 59634051HCID 59634051, Verbindung2×

Produkt 1

HCID 59633933HCID 59633933, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×HCID 178419050HCID 178419050, VerbindungLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a suspension of zinc (3.0 g) and lithium chloride (1.5 g) in THF (25 mL) were added dibromoethane (0.30 mL) and chlorotrimethylsilane (0.44 mL) at 70° C. under argon atmosphere. The mixture was stirred at 70° C. for 10 min. A solution of 1-Boc-3-iodoazetidine (9.8 g) in THF (10 mL) was added dropwise to the mixture at RT. The mixture was stirred at RT for 1 hr. To the mixture were added a solution of 1-(4-cyclopropylbenzyloxy)-4-iodo-2-methoxybenzene (5.3 g) prepared in (3) in THF (15 mL) and bis(triphenylphosphine)palladium (II) dichloride (0.49 g). The reaction mixture was stirred at RT for 3 hr. The reaction mixture was quenched with saturated aqueous NH4C1 and extracted with ethyl acetate. The organic layer was dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by silica-gel chromatography (Developing solvent: hexane/ethyl acetate=9/1 to 4/1) to give the title compound.

Aufarbeitung

  1. stirringThe mixture was stirred at RT for 1 hr
  2. stirringThe reaction mixture was stirred at RT for 3 hr
  3. customThe reaction mixture was quenched with saturated aqueous NH4C1
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over MgSO4
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by silica-gel chromatography (Developing solvent: hexane/ethyl acetate=9/1 to 4/1)

Quellen und Nachweise

ORD-Eintrag
ord-4264a397a6c64c33ab8867c63fcb3112
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765739B2

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