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

HRID 1626857Notes

Reaction equation

HRID 1626857 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[CH:8][C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:2]1=2.[H-].[Na+].I[CH3:20]>CN(C=O)C.O>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[CH:8][C:9]([CH:11]([CH3:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:2]1=2

Participants

6

Reactant 3

HCID 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 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of Ethyl 2-(2,3-dihydrobenzo[b][1,4]dioxin-7-yl)acetate (257 mg, 1.16 mmol) in DMF (2 mL) was added NaH (50 mg, 1.25 mmol) and iodomethane (167 mg, 1.18 mmol) in DMF (0.5 mL) at 0° C. The reaction mixture was stirred for 1 hrs at 0° C. then diluted with H2O (20 mL) and extracted with EtOAc (20 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:6) as eluant.

Workup

  1. extractionextracted with EtOAc (20 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-4d9c01849b17477faef48f4b384c5f01
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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