Chloromethyl Methyl Ether → HCID 11557648, compound

HRID 1854655Notes

Reaction equation

HRID 1854655 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(N(CC)C(C)C)(C)C.[CH3:20][O:21][CH2:22]Cl.[C:24]([O:27][CH2:28]C)(=O)C>ClCCl.CN(C)C1C=CN=CC=1.Cl>[CH3:20][O:21][CH2:22][O:1][C:2]1[C:9]([O:10][CH2:24][O:27][CH3:28])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

8

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 905792,3-Dihydroxybenzaldehyde

Product 1

HCID 11557648HCID 11557648, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

2,3-Dihydroxybenzaldehyde (300 mg, 2.17 mmol) was placed in a 20 mL reaction vessel, and dissolved in 6.5 mL of dry dichloromethane. To the solution were added N,N-diisopropylethylamine (1.1 mL, 6.3 mmol), 4-dimethylaminopyridine (13 mg, 0.11 mmol), and chloromethyl methyl ether (412 μL, 5.43 mmol). After being stirred at room temperature overnight, the reaction mixture was diluted with 100 mL of ethyl acetate and 20 mL of 1N HCl, and extracted. The extract was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a colorless oil (400 mg, 81%).

Workup

  1. extractionextracted
  2. washThe extract was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e0e12311dc2f4959bf847a8b5f1f11e3
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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