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

HRID 1091858Notes

Reaction equation

HRID 1091858 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 61.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a well stirred solution of 7-methoxy-2-methylbenzo[b]furan (72 g, 0.443 moles) in DCM (1.5 L) was added stannous chloride (150.3 g, 0.577 moles) followed by slow addition of 1,1-dichloromethyl methyl ether (56.1 g, 0.488 moles) at −10-0° C. and stirred for 1-2 hrs. Ice cold water (1.0 L) was added with vigorous stirring, the organic layer was separated and washed with water (2×550 mL) and dried over anhydrous sodium sulfate. Removal of solvent gave crude product (68.0 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 (52 g).

Workup

  1. customthe organic layer was separated
  2. washwashed with water (2×550 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customRemoval of solvent
  5. customgave crude product (68.0 g)
  6. customThe crude product was purified by silica gel column

Sources & evidence

ORD record
ord-aa16118b55aa4f9b9beb1d420c6c6756
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

Loading…