Dimethylformamide → [4-Cyano-5-methyl-4-(2-formyl-5-thienyl)hexyloxy]-t-butyldimethyl Silane

HRID 1582771Notes

Reaction equation

HRID 1582771 reaction equation
[C:1]([C:3]([C:18]1[S:22][C:21](Br)=[CH:20][CH:19]=1)([CH:15]([CH3:17])[CH3:16])[CH2:4][CH2:5][CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])#[N:2].C([Li])CCC.CN(C)[CH:31]=[O:32].[Cl-].[NH4+]>O1CCCC1.CCCCCC.[Cl-].[Na+].O>[C:1]([C:3]([C:18]1[S:22][C:21]([CH:31]=[O:32])=[CH:20][CH:19]=1)([CH:15]([CH3:17])[CH3:16])[CH2:4][CH2:5][CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])#[N:2]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 22393724[4-Cyano-5-methyl-4-(2-bromo-5-thienyl)hexyloxy]-tert-butyldimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 22718248[4-Cyano-5-methyl-4-(2-formyl-5-thienyl)hexyloxy]-t-butyldimethyl Silane

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of [4-cyano-5-methyl-4-(2-bromo-5-thienyl)hexyloxy]-t-butyldimethyl silane, 1.42 g 3.41 mmol, in tetrahydrofuran 20 ml was cooled to −70° C. A solution of 1.53 M butyl lithium in hexane 1.52 ml was added dropwise thereto and stirred for 10 minutes. N,N-dimethylformamide 1.52 ml was added thereto, and the temperature was raised to room temperature. Aqueous saturated ammonium chloride and brine were added to the reaction mixture which was then extracted with ether. The organic layer was washed with brine, dried over magnesium sulfate anhydride and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 515 mg 1.41 mmol, 41.3%, was obtained as a yellow syrup.

Workup

  1. extractionwas then extracted with ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate anhydride
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 515 mg 1.41 mmol, 41.3%
  6. customwas obtained as a yellow syrup

Sources & evidence

ORD record
ord-4b64be1cd62d4c03a10e539393a91cf0
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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