Ethanol → HCID 67259967, compound

HRID 1467692Notes

Reaction equation

HRID 1467692 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]([C:19]2[CH:27]=[CH:26]C=C3[C:20]=2[CH2:21][O:22]C3=O)[C:9](=[O:18])[C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[O-]S([O-])(=O)=O.[Na+].[Na+].[O-]CC.[Na+].C(O)C.[C:45]([O:49][CH2:50][CH3:51])(=[O:48])[CH2:46][CH3:47]>>[OH:22][C:21]1[C:20]2[C:46]([C:45]([O:49][CH2:50][CH3:51])=[O:48])=[CH:47][CH:26]=[CH:27][C:19]=2[N:8]([CH2:7][C:6]2[CH:29]=[CH:30][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9](=[O:18])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 7749Ethyl PropionateHCID 24436Sodium SulfateHCID 2723922Sodium ethoxideHCID 67258482HCID 67258482, compound

Product 1

HCID 67259967HCID 67259967, compoundYield 80%

Conditions

Temperature
0 °C

Procedure

A mixture of N-(4-methoxybenzyl)-2-oxo-N-(1-oxo-1,3-dihydroisobenzofuran-4-yl)-2-phenylacetamide (4.7 g, 11.7 mmol) and anhydrous Na2SO4 (16.6 g, 117 mmol) in anhydrous ethyl propionate (120 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (673 mg, 29.2 mmol) in anhydrous ethanol (70 mL)) was added dropwise. After the addition, the mixture was stirred at room temperature for 18 hr. The mixture was quenched with water (100 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (250 mL×4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give product (4.02 g, yield 80%). LC-MS (ESI) m/z: 430 (M+1)+. 1H-NMR (400 MHz, DMSO-d) δ (ppm): 1.23-1.26 (t, J=6.8 Hz, 3H), 3.69 (s, 3H), 4.21-4.23 (m, 2H), 5.46 (s, 1H), 6.86-6.88 (d, J=7.6 Hz, 2H), 7.11-7.18 (m, 3H), 7.36-7.55 (m, 7H), 10.59 (s, 1H).

Workup

  1. additionAfter the addition
  2. customThe mixture was quenched with water (100 mL) and solvent
  3. customwas removed in vacuum
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate (250 mL×4)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7dc492bce9284415a7ae2076f8408f36
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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