Dimethylformamide → 5-Methoxy-2,3-dihydrobenzofuran-6-carbaldehyde

HRID 1740513Notes

Reaction equation

HRID 1740513 reaction equation
Br[C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[CH:3]=1.C([Li])CCC.CN([CH:21]=[O:22])C>C1COCC1>[CH3:12][O:11][C:10]1[C:2]([CH:21]=[O:22])=[CH:3][C:4]2[O:8][CH2:7][CH2:6][C:5]=2[CH:9]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 154539206-Bromo-5-methoxy-2,3-dihydrobenzofuranHCID 178418339Butyllithium

Product 1

HCID 100124745-Methoxy-2,3-dihydrobenzofuran-6-carbaldehydeYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-5-methoxy-2,3-dihydrobenzofuran (9.20 g, 40.35 mmol) in THF (50 mL) was dropwise added n-Butyl lithium (24.00 mL, 38.40 mmol) at -78° C. After stirring for 30 min, DMF (5.00 ml, 60.53 mmol) was added and the mixture was allowed to stir at room temperature for 2 h. The reaction was quenched with water and extracted with ethyl acetate (3×150 mL). The combined organic extracts were dried (Na2SO4) and the solvent was removed under reduced pressure. Flash chromatography (1:1 ether/hexane) of the residue afforded 5.42 g (76%) of the title compound as a yellow solid: 1H NMR (250 MHz, CDCl3) d 10.32 (s, 1H), 6.90 (s, 1H), 6.82 (s, 1H), 4.57 (t, 2H), 3.91 (s, 3H), 3.25 (t, 2H).

Workup

  1. customat -78° C
  2. stirringto stir at room temperature for 2 h
  3. customThe reaction was quenched with water
  4. extractionextracted with ethyl acetate (3×150 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-33228f594100472da7ad5237ced6a139
Source dataset
uspto-grants-1999_10
Patent number
US05969151

Reaction notes

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