Tributylstannane → HCID 11733611, compound

HRID 1053898Notes

Reaction equation

HRID 1053898 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH2:9]([SnH:13]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH3:12].[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=1.Cl[C:33]([O:35][CH3:36])=[O:34]>O1CCCC1>[C:33](=[O:34])([O:35][CH3:36])[O:29][CH:28]([C:27]1[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=1)[Sn:13]([CH2:9][CH2:10][CH2:11][CH3:12])([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 5948TributylstannaneHCID 6586Methyl chloroformateHCID 312444-MethoxybenzaldehydeHCID 2724682Lithium diisopropylamide

Product 1

HCID 11733611HCID 11733611, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To dry tetrahydrofuran (80 mL) cooled to −78° C. was added a solution of lithium diisopropylamide (2.0 M in heptane/tetrahydrofuran/ethylbenzene, 18.36 mL, 37.5 mmol) followed by tri-n-butyltin hydride (9.81 mL, 37.5 mmol) dropwise. After 5 minutes, the mixture was placed in an ice water bath for 0.5 hours, then recooled to −78° C. 4-Methoxybenzaldehyde (4.45 mL, 37.5 mmol) was added dropwise, and the reaction mixture was stirred at this temperature for 1.5 hours. Afterwards, methyl chloroformate (3.41 mL, 44.1 mmol) was added dropwise, the cooling bath was removed, and the mixture was allowed to stir overnight at room temperature. Then a solution of saturated aqueous ammonium chloride (100 mL) was added followed by extraction with ethyl acetate. The organic extract was dried, filtered and concentrated. The residue was purified by chromatography (silica gel, ethyl acetate in hexanes) which afforded 6.7 g, (38%) of the title compound.

Workup

  1. waitthe mixture was placed in an ice water bath for 0.5 hours
  2. customrecooled to −78° C
  3. customthe cooling bath was removed
  4. stirringto stir overnight at room temperature
  5. additionThen a solution of saturated aqueous ammonium chloride (100 mL) was added
  6. extractionfollowed by extraction with ethyl acetate
  7. extractionThe organic extract
  8. customwas dried
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by chromatography (silica gel, ethyl acetate in hexanes) which

Sources & evidence

ORD record
ord-f3183fe53ceb4883b222d4d4e79a6ef9
Source dataset
uspto-grants-2016_07
Patent number
US09394279B2

Reaction notes

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