2-Thienylacetonitrile → HCID 22393615, compound

HRID 1071613Notes

Reaction equation

HRID 1071613 reaction equation
[BH4-].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][C:9]#[N:10].BrC[CH2:13][CH2:14][O:15][Si](C(C)(C)C)(C)C>CN(C=O)C>[C:9]([CH:8]([C:4]1[S:3][CH:7]=[CH:6][CH:5]=1)[CH2:13][CH2:14][OH:15])#[N:10]

Participants

5

Reactant 3

HCID 728802-ThienylacetonitrileHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 4311764Sodium borohydride

Product 1

HCID 22393615HCID 22393615, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, sodium borohydride (650 mg) was added in an ice bath to a DMF solution (25 ml) of thiophene-2-acetonitrile (1 g) and (3-bromopropoxy)-tert-butyldimethylsilane (2.06 g). After 20 minutes, the organic layer was separated by adding an aqueous saturated ammonium chloride and ethyl acetate were added thereto. The resulting organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. After filtering off the drying agent, the mixture was evaporated. The resulting residue was dissolved in acetonitrile (20 mL), a 1 M tetrabutylammonium fluoride/tetrahydrofuran solution (9.7 ml) was added thereto, and the mixture was stirred at a room temperature. After 18 hours, the organic layer was separated by adding water and ethyl acetate. The resulting organic layer was rinsed with water and brine, and dried over magnesium sulfate. After filtering off the drying agent, the mixture was evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate system), to give the title compound as a red oil (637 mg, 43%). 1H-NMR (400 MHz, CDCl3) δ 2.08-2.16 (m, 1H), 3.08 (t, J=7.0 Hz, 2H), 3.75 (t, J=7.0 Hz, 2H), 4.15-4.20 (m, 1H), 7.14 (dd, J=3.8 Hz, 4.8 Hz, 1H), 7.65 (dd, J=0.8 Hz, 4.8 Hz, 1H), 7.75 (dd, J=0.8 Hz, 3.8 Hz, 1H).

Workup

  1. customthe organic layer was separated
  2. additionby adding an aqueous saturated ammonium chloride and ethyl acetate
  3. additionwere added
  4. washThe resulting organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering off the drying agent
  7. customthe mixture was evaporated
  8. dissolutionThe resulting residue was dissolved in acetonitrile (20 mL)
  9. additiona 1 M tetrabutylammonium fluoride/tetrahydrofuran solution (9.7 ml) was added
  10. waitAfter 18 hours
  11. customthe organic layer was separated
  12. additionby adding water and ethyl acetate
  13. washThe resulting organic layer was rinsed with water and brine
  14. dry with materialdried over magnesium sulfate
  15. filtrationAfter filtering off the drying agent
  16. customthe mixture was evaporated
  17. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate system)

Sources & evidence

ORD record
ord-7b862c3c6cd04bca9f579c005408f2ac
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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