Hydrochloric Acid → HCID 57545176, compound

HRID 1928862Notes

Reaction equation

HRID 1928862 reaction equation
[OH:1][C:2]1[C:7]2[C:8](=[O:11])[CH2:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][O:21][CH3:22].Cl>CN(C)C=O>[CH3:22][O:21][CH2:20][CH2:19][O:1][C:2]1[C:7]2[C:8](=[O:11])[CH2:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 11949510HCID 11949510, compound

Product 1

HCID 57545176HCID 57545176, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-hydroxy-benzofuran-3-one (CAS no: 19278-81-0) (4.9 g, 9 mmol), potassium carbonate (1.66 g, 12 mmol) and 2-bromoethyl methylether (1.13 mL, 12 mmol) in N,N-dimethylformamide (20 mL) was stirred at 80° C. for 1.5 h. Cooled to 23° C., poured into 1 N HCl, extracted four times with ethyl acetate, dried combined organic layer over Na2SO4. Removal of the solvent in vacuum left a yellow residue which was purified by silica gel column chromatography with heptane/ethyl acetate to give the title compound as a white solid (1.3 g, 63%); MS: m/e=177.2 (M−OMe+H+).

Workup

  1. temperatureCooled to 23° C.
  2. extractionextracted four times with ethyl acetate
  3. customdried
  4. customRemoval of the solvent in vacuum
  5. waitleft a yellow residue which
  6. customwas purified by silica gel column chromatography with heptane/ethyl acetate

Sources & evidence

ORD record
ord-14db04e28aef42099748bd0f8f4736e0
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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