Tetrahydrofuran → t-Butyl[(4-ethyl-2-thienyl)methoxy]dimethylsilane

HRID 2247683Notes

Reaction equation

HRID 2247683 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[S:5][CH:6]=1.[CH2:16]([Mg]Br)[CH3:17].O1CCCC1.[Cl-].[NH4+]>CCOCC.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:12]([Si:9]([O:8][CH2:7][C:4]1[S:5][CH:6]=[C:2]([CH2:16][CH3:17])[CH:3]=1)([CH3:11])[CH3:10])([CH3:15])([CH3:14])[CH3:13]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 10614666[(4-Bromo-2-thienyl)methoxy]t-butyldimethylsilaneHCID 178418443HCID 178418443, compound

Product 1

HCID 59052006t-Butyl[(4-ethyl-2-thienyl)methoxy]dimethylsilaneYield 95%

Reagents, catalysts & solvents 3

HCID 178418745HCID 178418745, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of [(4-bromo-2-thienyl)methoxy](t-butyl)dimethylsilane (0.61 g, 2.0 mmol) and [1,3-bis(diphenylphosphino)propane]dichloronickel (54 mg, 0.1 mmol) in ether (5 ml) was added slowly a 1.0 M solution of ethylmagnesium bromide in tetrahydrofuran (3.0 ml, 3.0 mmol) at 0° C. with stirring, and after raising the reaction temperature to room temperature, the resulting mixture was stirred for 1 hour. After stirring, a saturated aqueous solution of ammonium chloride (5 ml) was added to the reaction mixture to quench the reaction, and the resulting mixture was poured into water (20 ml) and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (0:10 to 5:95) as the eluent to afford the title compound (0.44 g) in a yield of 95% as a pale yellow oily product.

Workup

  1. stirringthe resulting mixture was stirred for 1 hour
  2. stirringAfter stirring
  3. customto quench
  4. customthe reaction
  5. extractionextracted with ether
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. filtrationAfter filtration
  9. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-0972488ed4f047a18c8c71e6b00b2178
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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