Dimethylformamide → HCID 18373033, compound

HRID 1601179Notes

Reaction equation

HRID 1601179 reaction equation
[C:1]([C:11]1[CH:19]=[CH:18][C:14]2[S:15][CH:16]=[CH:17][C:13]=2[CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C([Li])CCC.CN(C)[CH:27]=[O:28]>CCOCC>[C:1]([C:11]1[CH:19]=[CH:18][C:14]2[S:15][C:16]([CH:27]=[O:28])=[CH:17][C:13]=2[CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 18373051HCID 18373051, compoundHCID 178418339Butyllithium

Product 1

HCID 18373033HCID 18373033, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 5-(1-decynyl)benzo[b]thiophene (20.0 g) in dry ether (150 ml), under nitrogen, was added n-butyllithium (2.5 M in hexanes) (32.6 ml) dropwise, with stirring at room temperature. The solution was stirred at room temperature, under nitrogen, for 2.5 hrs and then cooled to -60° C. A solution of dry dimethylformamide (5.95 g) in dry ether (15 ml) was added dropwise, and the reaction mixture was allow to warm to room temperature. The reaction mixture was quenched with ammonium chloride solution and the layers separated. The aqueous phase was extracted with ether, the organic extracts combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated. The residue was flash chromatographed (silica: 3-4%, ethyl acetate:heptane). The appropriate fractions were collected and evaporated. The residue was recrystallized from heptane to give 11.5 g (52.0%) of product, mp 45-47° C.

Workup

  1. stirringThe solution was stirred at room temperature, under nitrogen, for 2.5 hrs
  2. temperaturecooled to -60° C
  3. temperatureto warm to room temperature
  4. customThe reaction mixture was quenched with ammonium chloride solution
  5. customthe layers separated
  6. extractionThe aqueous phase was extracted with ether
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe filtrate was evaporated
  10. customchromatographed (silica: 3-4%, ethyl acetate:heptane)
  11. customThe appropriate fractions were collected
  12. customevaporated
  13. customThe residue was recrystallized from heptane

Sources & evidence

ORD record
ord-84439d771ac54cdd95b7a667ee104139
Source dataset
uspto-grants-1999_11
Patent number
US05977147

Reaction notes

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