Tetrahydrofuran → HCID 66958338, compound

HRID 1362550Notes

Reaction equation

HRID 1362550 reaction equation
[C:1]1([CH:7]=[CH:8][C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC(=O)[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=1)=[CH2:16].[C:25]([O-:28])(O)=[O:26].[Na+].O1CCC[CH2:31]1>O>[CH3:31][O:28][C:25](=[O:26])[CH:16]=[CH:15][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:9](=[O:10])[CH:8]=[CH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:18]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 660233-Phenylprop-2-enoyl chlorideHCID 516892Sodium BicarbonateHCID 57495369m-Aminophenylacrylic acid methyl ester

Product 1

HCID 66958338HCID 66958338, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of phenylacryloylchloride (0.47 g, 2.85 mmol) (Acros) in tetrahydrofuran (10.0 ml) was added to a mixture of m-aminophenylacrylic acid methyl ester (7) (0.44 g, 2.50 mmol) in tetrahydrofuran (15.0 ml) and NaHCO3 (0.37 g, 4.50 mmol) in water (8.0 ml), and the resultant solution was stirred at room temperature for one hour. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 2N HCl. The organic layer was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was removed and the residue was chromatographed on silica gel with petroleum ether-ethyl acetate (2:1, v/v) as eluent. The obtained product was washed with diethyl ether to give the title compound (0.54 g, 70%). 1H NMR (DMSO-d6, HMDSO), δ: 3.72 (3H, s); 6.52 (1H, d, J=16.0 Hz); 6.83 (1H, d, J=16.0 Hz); 7.29-7.85 (10H, m); 7.98 (1H, br s); 10.32 (1H, br s).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and 2N HCl
  3. washThe organic layer was washed successively with water, saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed
  6. customthe residue was chromatographed on silica gel with petroleum ether-ethyl acetate (2:1
  7. washThe obtained product was washed with diethyl ether

Sources & evidence

ORD record
ord-ecbd7d21b4784336a04129beb2b8488d
Source dataset
uspto-grants-2011_02
Patent number
US07880020B2

Reaction notes

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