Carbon Dioxide → HCID 69170253, compound

HRID 1028469Notes

Reaction equation

HRID 1028469 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([O:7][C:8]2[S:9][CH:10]=[CH:11][N:12]=2)=[CH:5][CH:4]=1.C([Li])CCC.[CH2:20]([Sn:24](Cl)([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23].C(=O)=O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([O:7][C:8]2[S:9][C:10]([Sn:24]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:20][CH2:21][CH2:22][CH3:23])=[CH:11][N:12]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 15096Tributyltin ChlorideHCID 69170730HCID 69170730, compoundHCID 178418339Butyllithium

Product 1

HCID 69170253HCID 69170253, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 11A (3.27 g, 15.8 mmol) in tetrahydrofuran (30 mL) was added n-butyl lithium (2.5 M in hexanes, 6.50 mL, 16.3 mmol, 1.0 eq.) at −78° C. The mixture was stirred for 1 hour. Tributyltin chloride (4.40 mL, 16.3 mmol, 1.0 eq) was then added at −78° C. (The dry ice bath was removed and the mixture was stirred for 1 hour. The reaction was quenched with water (100 mL). The aqueous layer was extracted with ether and the organic layer washed with brine, dried over MgSO4 and concentrated. The residue was purified on silica gel eluting with ethyl acetate: hexane gradient (0-20%) to give the title compound (7.07 g, 92%).

Workup

  1. customwas removed
  2. stirringthe mixture was stirred for 1 hour
  3. customThe reaction was quenched with water (100 mL)
  4. extractionThe aqueous layer was extracted with ether
  5. washthe organic layer washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-07ff4b09093d43fba5a969c2a1bc2a6f
Source dataset
uspto-grants-2014_05
Patent number
US08735595B2

Reaction notes

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