Methane, dichloromethoxy- → 7-Methoxy-2-methyl-1-benzofuran-4-carbaldehyde

HRID 548967Notes

Reaction equation

HRID 548967 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]([CH3:12])=[CH:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:13][O:14]C(Cl)Cl>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]([CH3:12])=[CH:11][C:7]=2[C:6]([CH:13]=[O:14])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 112751777-Methoxy-2-methylbenzofuran

Product 1

HCID 110415447-Methoxy-2-methyl-1-benzofuran-4-carbaldehydeYield 30.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a well stirred solution of 7-methoxy-2-methylbenzo[b]furan (from step 2) (6.5 g, 40.07 mmol) in DCM (70.0 mL) was added stannous chloride (17.7 g, 68.26 mmol) followed by slow addition of 1,1-dichloromethyl methyl ether (4.6 g, 40.07 mmol) at −10-0° C. and stirred for 1-2 hrs. Ice cold water (100 mL) was added with vigorous stirring, the organic layer was separated and washed with water (2×50 mL) and dried over anhydrous sodium sulfate. Removal of solvent gave crude product (7.0 g). The crude product was purified by silica gel column using petroleum ether:ethyl acetate (9:1) as an eluent to afford the product as pale yellow oil (2.3 g).

Workup

  1. customthe organic layer was separated
  2. washwashed with water (2×50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customRemoval of solvent
  5. customgave crude product (7.0 g)
  6. customThe crude product was purified by silica gel column

Sources & evidence

ORD record
ord-5f08eb1c966b4a0aa83e5176b57a883a
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

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