Tetrahydrofuran → HCID 49804856, compound

HRID 1627906Notes

Reaction equation

HRID 1627906 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]2[S:9][C:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[C:6]2=[C:5]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[C:4]=1[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:39]1[CH2:43]OC[CH2:40]1.C(I)CC>CN(C=O)C>[CH2:1]([C:3]1[N:8]=[C:7]2[S:9][C:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[C:6]2=[C:5]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[C:4]=1[CH:23]([CH2:40][CH2:39][CH3:43])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 336431-IodopropaneHCID 2733832Lithium HexamethyldisilazideHCID 49804857Ethyl [2-ethyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetate

Product 1

HCID 49804856HCID 49804856, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl [2-ethyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetate (0.491 g; 1.25 mmol) in dry DMF (5 mL) at −10° C. was added a 1N solution of LHMDS in THF (1.38 mL; 1.38 mmol) and 1-propyliodide (0.183 mL; 1.88 mmol). The reaction mixture was allowed to warm up to room temperature and the stirring was carried on for 3 h. The reaction mixture was quenched by addition of a saturated solution of ammonium chloride and the mixture was extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to afford 0.322 g (59%) of the title compound as a light yellow oil.

Workup

  1. customwas carried on for 3 h
  2. customThe reaction mixture was quenched by addition of a saturated solution of ammonium chloride
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f102c75afb274ac19f8fa69d303bec21
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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