Ethyl Acetate → HCID 71245549, compound

HRID 532127Notes

Reaction equation

HRID 532127 reaction equation
[Cl-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][CH:8]([NH3+:14])[C:7]2=[O:15].C(N(C(C)C)CC)(C)C.[C:25]([O:28][CH2:29][CH3:30])(=[O:27])C>O1CCCC1>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][CH:8]([NH:14][C:25](=[O:27])[O:28][CH2:29][CH3:30])[C:7]2=[O:15]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 86676468HCID 86676468, compound

Product 1

HCID 71245549HCID 71245549, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2.82 g (12.3 mmol) of 6-methoxy-4-oxochroman-3-aminium chloride were dissolved in tetrahydrofuran under nitrogen atmosphere and cooled to 0° C. with an ice bath. Diisopropylethylamine and ethyl carbononochloridate were added. The mixture was allowed to warm to room temperature and stirred for 30 min. The mixture was diluted with ethyl acetate and washed with saturated ammonium chloride solution (2×) and water (1×). The organic phase was washed dried over MgSO4, and concentrated in vacuo to give 3.5 g (13.2 mmol, quant.) of crude material.

Workup

  1. temperatureto warm to room temperature
  2. washwashed with saturated ammonium chloride solution (2×) and water (1×)
  3. washThe organic phase was washed
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give 3.5 g (13.2 mmol, quant.) of crude material

Sources & evidence

ORD record
ord-8a52d100f2b6419a9581e43fa909f9d8
Source dataset
uspto-grants-2014_10
Patent number
US08853196B2

Reaction notes

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