Methyl iodide → Methyl 6-methoxy-2,3-dihydro-benzo[1,4]dioxine

HRID 2266126Notes

Reaction equation

HRID 2266126 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].[O:7]1[C:12]2[CH:13]=[CH:14][C:15](O)=[CH:16][C:11]=2[O:10][CH2:9][CH2:8]1.I[CH3:19]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CN(C=O)C>[CH3:19][CH:9]1[O:10][C:11]2[CH:16]=[CH:15][C:14]([O:4][CH3:1])=[CH:13][C:12]=2[O:7][CH2:8]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 91152732,3-Dihydro-1,4-benzodioxin-6-ol

Product 1

HCID 21624819Methyl 6-methoxy-2,3-dihydro-benzo[1,4]dioxineYield 85%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of K2CO3 (47.54 g, 344 mmol) and Bu4NI (1.256 g, 3.4 mmol) in DMF was added 2,3-dihydro-benzo[1,4]dioxin-6-ol (26.2 g, 172 mmol) followed by iodomethane (16.1 ml, 258 mmol). After 16 hours the mixture was filtered. The solution was mixed with H2O and extracted with ethyl acetate. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification via flash chromatography (95:5 hexane/ethyl acetate) afforded methyl 6-methoxy-2,3-dihydro-benzo[1,4]dioxine (24.23 g, 85%) as a clear oil.

Workup

  1. filtrationAfter 16 hours the mixture was filtered
  2. additionThe solution was mixed with H2O
  3. extractionextracted with ethyl acetate
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification via flash chromatography (95:5 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4cc26b59ebac421aab9a365e15a04b37
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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