Tetrahydrofuran → HCID 137328929, compound

HRID 1296008Notes

Reaction equation

HRID 1296008 reaction equation
[C:1]([C:5]1([SiH2:11][C:12]([O:27][C:28]([C:47]2[CH:48]=[N:49][C:50](Cl)=[CH:51][CH:52]=2)([SiH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[SiH2:29][C:30]2([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH2:31]2)([C:20]2[CH:21]=[N:22][C:23](Cl)=[CH:24][CH:25]=2)[SiH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH:54]1([Mg]Br)[CH2:56][CH2:55]1.[NH4+].[Cl-].O1[CH2:65][CH2:64][CH2:63]C1>>[C:1]([C:5]1([SiH2:11][C:12]([O:27][C:28]([C:47]2[CH:48]=[N:49][C:50]([CH:63]3[CH2:64][CH2:65]3)=[CH:51][CH:52]=2)([SiH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[SiH2:29][C:30]2([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH2:31]2)([C:20]2[CH:21]=[N:22][C:23]([CH:54]3[CH2:56][CH2:55]3)=[CH:24][CH:25]=2)[SiH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 137328927HCID 137328927, compoundHCID 178418630HCID 178418630, compound2×

Product 1

HCID 137328929HCID 137328929, compound

Procedure

NiCl2(dppf)2 (0.45 g, 0.66 mmol) was added to a solution of 1-(tert-butyl)-1,1-diphenylsilyl [(6-chloro-3-pyridyl)methyl]ether (5.0 g, 13 mmol) in tetrahydrofuran (26 ml) at room temperature, after which 1.0 M cyclopropylmagnesium bromide (16 ml) was slowly added dropwise and stirring was continued at room temperature for 5.5 hours. Next, 1.0 M cyclopropylmagnesium bromide (10 ml) was slowly added dropwise over a period of 1.5 hours and stirring was continued for 15 hours. Saturated aqueous NH4Cl was added, and then the mixture was stirred for 3 hours and filtered through celite and extraction was performed with ethyl acetate. After drying with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (1.3 g) as a mixture with impurities. This product was used without further purification for the following reaction.

Workup

  1. stirringstirring
  2. waitwas continued for 15 hours
  3. stirringthe mixture was stirred for 3 hours
  4. filtrationfiltered through celite and extraction
  5. dry with materialAfter drying with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4da510cc329c4423954b672f76462232
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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