Dimethylformamide → HCID 86719446, compound

HRID 589218Notes

Reaction equation

HRID 589218 reaction equation
[CH2:1]([Si:4]([CH2:18][CH:19]=[CH2:20])([CH2:15][CH:16]=[CH2:17])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1)[CH:2]=[CH2:3].C([Mg]Cl)(C)C.[Li]CCCC.CN(C)[CH:33]=[O:34].[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[CH2:1]([Si:4]([CH2:18][CH:19]=[CH2:20])([CH2:15][CH:16]=[CH2:17])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:33]=[O:34])=[CH:10][CH:9]=1)[CH:2]=[CH2:3]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 86719447HCID 86719447, compoundHCID 178418339ButyllithiumHCID 178418918HCID 178418918, compound

Product 1

HCID 86719446HCID 86719446, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

Under a nitrogen atmosphere, to 4-{3-(triallylsilyl)propyl}phenyl bromide (3) (14.2 g, 40.6 mmol), tetrahydrofuran (THF) (50 ml) was added, cooled to −10° C. using salt ice. 2M of iPrMgCl solution (0.70 equiv., 14.2 ml) and 1.67M of nBuLi solution (1.4 equiv., 34.0 ml) were each added dropwise, then stirred at around −10° C. for 2 hours. N,N-dimethylformamide (DMF) (2 equiv., 6.3 ml) was added and stirred at room temperature for 14 hours. To the reacted mixture, diethyl ether was added and then neutralized with saturated ammonium chloride aqueous solution. The obtained water layer was extracted with diethyl ether, the collected organic layer was washed with saturated saline solution then dried over anhydrous magnesium sulfate, then filtered and concentrated under reduced pressure, obtaining a crude product. The crude product was separated and purified using silica gel column chromatography (eluent: hexane/ethyl acetate=20/1), obtaining 4-{3-(triallylsilyl)propyl}benzaldehyde (4) represented by the following chemical formula (yield: 11.0 g, yield (%): 89%).

Workup

  1. additioneach added dropwise
  2. stirringstirred at room temperature for 14 hours
  3. extractionThe obtained water layer was extracted with diethyl ether
  4. washthe collected organic layer was washed with saturated saline solution
  5. dry with materialthen dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customobtaining a crude product
  9. customThe crude product was separated
  10. custompurified

Sources & evidence

ORD record
ord-9e2947d63ead4301a4f31fd449c6b5a4
Source dataset
uspto-grants-2016_01
Patent number
US09228107B2

Reaction notes

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