Dimethylformamide → 3-Isopropylbenzofuran-2-carbaldehyde

HRID 1362399Notes

Reaction equation

HRID 1362399 reaction equation
[CH:1]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH:5]=1)([CH3:3])[CH3:2].[Li]CCCC.CN([CH:21]=[O:22])C>C1COCC1>[CH:1]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[CH:21]=[O:22])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 112174123-IsopropylbenzofuranHCID 178418339Butyllithium

Product 1

HCID 577420813-Isopropylbenzofuran-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 3-isopropylbenzofuran (250 mg, 1.56 mmol) in THF (1 mL) is added nBuLi (2 mL, 2 mmol) drop wise and the reaction is stirred for 30 minutes. DMF (1 mL) was added to the reaction and stirred at room temperature overnight. The solution is placed in an ice bath and carefully quenched with 5% aqueous HCl solution (2 mL), and extracted with ethyl acetate (3×5 mL), dried over sodium sulfate and concentrated. The product was purified on silica with 100% hexanes to yield title compound in as a colorless oil (250 mg, 85%): 1H NMR (400 MHz, CDCl3) δ 10.10 (s, 1H), 7.78 (d, 1H, J=9.0 Hz), 7.55 (d, 1H, J=9.0 Hz), 7.32-7.24 (m, 2H), 3.11-3.07 (m, 1H), 1.33-1.31 (2s, 6H).

Workup

  1. stirringstirred at room temperature overnight
  2. customThe solution is placed in an ice bath
  3. customcarefully quenched with 5% aqueous HCl solution (2 mL)
  4. extractionextracted with ethyl acetate (3×5 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified on silica with 100% hexanes

Sources & evidence

ORD record
ord-6fc955e1185a4719ae21bbc3218b853c
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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