Hydrochloric Acid → Ethyl 2-(2,3-dihydrobenzo[b][1,4]dioxin-7-yl)propanoate

HRID 1870840Notes

Reaction equation

HRID 1870840 reaction equation
[H-].[Na+].[CH2:3]1[CH2:12][O:11][C:10]2[CH:9]=[CH:8][C:7]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][C:5]=2[O:4]1.[CH3:19]I.Cl>CN(C)C=O>[O:11]1[C:10]2[CH:9]=[CH:8][C:7]([CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][C:5]=2[O:4][CH2:3][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18693373HCID 18693373, compound

Product 1

HCID 18693671Ethyl 2-(2,3-dihydrobenzo[b][1,4]dioxin-7-yl)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, 60% sodium hydride (1.13 g) was added to a solution in N,N-dimethylformamide (65 ml) of ethyl 3,4-ethylenedioxyphenylacetate [M. Sasamoto, Chem. Pharm. Bull., 8, 324 (1969)] (6.00 g) in an ice bath. Thereafter, methyl iodide (1.76 ml) was added dropwise and the resulting mixture was stirred under ice-cooling for 4 hours. To the reaction mixture was added 1 N hydrochloric acid and the resulting mixture was subjected to extraction with diethyl ether, after which the extraction solution was washed with water and then dried. The solvent was removed by distillation under reduced pressure and the residue was purified by a silica gel column chromatography to obtain the desired compound (5.57 g).

Workup

  1. temperaturecooling for 4 hours
  2. extractionthe resulting mixture was subjected to extraction with diethyl ether
  3. washafter which the extraction solution was washed with water
  4. customdried
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-7c1478ef702543129beb25360b0c3257
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

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