Triethylsilane → HCID 18472193, compound

HRID 566025Notes

Reaction equation

HRID 566025 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13](=O)[CH2:14][CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+].CC1C=CC(C2SC(CCCCC(OCC)=O)=CC=2)=CC=1.[OH-].[Na+]>FC(F)(F)C(O)=O.O1CCCC1.O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

10

Reactant 5

HCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 18472288HCID 18472288, compoundHCID 18472605HCID 18472605, compound

Product 1

HCID 18472193HCID 18472193, compoundYield 73.8%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 5-[5-(4-methylphenyl)thiophen-2-yl]-5-oxovalerate (4.50 g) in trifluoroacetic acid (7.66 ml) was added triethylsilane (5.7 ml) at room temperature, and the mixture was stirred for 4 days. To the reaction mixture was added ethyl acetate, and the mixture was made alkaline with saturated sodium bicarbonate solution. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:9) to give crude ethyl 5-[5-(4-methyl-phenyl)thiophen-2-yl]valerate. To a solution of the crude ethyl 5-[5-(4-methylphenyl)thiophen-2-yl]valerate in tetrahydrofuran (50 ml) was added 1N sodium hydroxide (20 ml) at room temperature, and the mixture was stirred for 24 hours. To the reaction mixture was added water, and the mixture was washed with diethylether. The aqueous layer was acidified with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure to precipitate crystals, which were collected by filtration and washed with hexane to give 5-[5-(4-methylphenyl)thiophen-2-yl]valeric acid (2.88 g) as colorless crystals.

Workup

  1. washThe organic layer was washed with saturated sodium chloride solution
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was separated
  5. custompurified with column chromatography (ethyl acetate/hexane=1:9)
  6. customto give crude ethyl 5-[5-(4-methyl-phenyl)thiophen-2-yl]valerate
  7. stirringthe mixture was stirred for 24 hours
  8. washthe mixture was washed with diethylether
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe organic layer was washed with saturated sodium chloride solution
  11. dry with materialdried with magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customto precipitate crystals, which
  14. filtrationwere collected by filtration
  15. washwashed with hexane

Sources & evidence

ORD record
ord-eb4cb92e373f4dfa9d14408c8ec74377
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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