Triethylamine → HCID 15037567, compound

HRID 466341Notes

Reaction equation

HRID 466341 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([Si:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].C(N(CC)CC)C.Cl[C:23]([C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1)=[O:24]>O1CCCC1>[C:25]1([C:23]([O:1][C:2]2[CH:7]=[C:6]([Si:8]([CH3:9])([CH3:10])[CH3:11])[CH:5]=[CH:4][C:3]=2[C:12](=[O:14])[CH3:13])=[O:24])[CH:26]=[CH:27][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 15037566HCID 15037566, compound

Product 1

HCID 15037567HCID 15037567, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling, to a solution of 832 mg (4 mmol) of 2'-hydroxy-4'-trimethylsilylacetophenone in 20 ml of tetrahydrofuran were added dropwise successively, 0.61 ml (4.4 mmol) of triethylamine and 874 mg (4.4 mmol) of methyl p-chloroformylbenzoate with stirring. The mixture was stirred at room temperature for 1 day and filtered. The filtrate was evaporated and the residue was dissolved in AcOEt. The organic solution was washed with H2O, aqueous sodium bicarbonate solution and brine, dried over anhydrous Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel [eluent: n-hexane-AcOEt (5:1)] to give 1.40 g of pale yellow viscous liquid (yield 95%).

Workup

  1. additionwere added dropwise successively
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. dissolutionthe residue was dissolved in AcOEt
  5. washThe organic solution was washed with H2O, aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel [eluent: n-hexane-AcOEt (5:1)]

Sources & evidence

ORD record
ord-1ce8e76948ad43809793603fd4866223
Source dataset
uspto-grants-1992_10
Patent number
US05155249

Reaction notes

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