Isopropylethylamine → HCID 10104420, compound

HRID 2103749Notes

Reaction equation

HRID 2103749 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.C(NCC)(C)C.CCCCCC.[C:25]([O:28][CH2:29]C)(=O)C.C(=O)(O)[O-].[Na+]>CN(C=O)C.COCCl>[CH3:25][O:28][CH2:29][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 88318IsopropylethylamineHCID 516892Sodium BicarbonateHCID 5281426UmbelliferoneHCID 21226206Ethyl acetate hexane

Product 1

HCID 10104420HCID 10104420, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7864Chloromethyl Methyl EtherSolvent

Procedure

Under an atmosphere of argon, to a solution of 7-hydroxycoumarine (100 g), isopropylethylamine (161 mL) in anhydrous DMF (500 mL), methoxymethyl chloride (70.3 mL) was dropped at 0° C. The mixture was stirred for 4 hours at room temperature. To the reaction mixture, a mixture of hexane/ethyl acetate (2/1), and a saturated aqueous solution of sodium bicarbonate were added, and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give the title compound (74.1 g) having the following physical data.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8422f316368c464288cfd8e89703bdfc
Source dataset
uspto-grants-2009_08
Patent number
US07576129B2

Reaction notes

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