Chloromethyl Methyl Ether → HCID 10104420, compound

HRID 1726324Notes

Reaction equation

HRID 1726324 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.[CH3:19][O:20][CH2:21]Cl.CCCCCC.C(OCC)(=O)C>CN(C)C=O>[CH3:19][O:20][CH2:21][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

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 88318IsopropylethylamineHCID 5281426UmbelliferoneHCID 21226206Ethyl acetate hexane

Product 1

HCID 10104420HCID 10104420, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-hydroxycoumarin (100 g) and isopropylethylamine (161 ml) in anhydrous dimethylformamide (DMF; 500 ml) was added dropwise methoxymethylchloride (70.3 ml) at 0° C. under an atmosphere of argon. The mixture was stirred at room temperature for 4 hours. To the reaction mixture were added hexane/ethyl acetate (2/1, 1000 ml) and a saturated aqueous solution of sodium bicarbonate (1000 ml) and the mixture was extracted twice with ethyl acetate. The organic layer was washewd with water (twice) 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. The obtained crude product was used to the next step without further purification.

Workup

  1. extractiona saturated aqueous solution of sodium bicarbonate (1000 ml) and the mixture was extracted twice with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-454e4ff045414ee29821d7db03787926
Source dataset
uspto-grants-2009_02
Patent number
US07491748B2

Reaction notes

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