Dimethylformamide → 2,3-Dihydro-1-benzofuran-7-carbaldehyde

HRID 1042358Notes

Reaction equation

HRID 1042358 reaction equation
[Li]C(CC)C.[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7]1.CN(C)CCN(C)C.CN([CH:26]=[O:27])C>C1COCC1>[O:6]1[C:10]2[C:11]([CH:26]=[O:27])=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 10329DihydrobenzofuranHCID 178418400CID 53628100

Product 1

HCID 27950182,3-Dihydro-1-benzofuran-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

sec-BuLi (20.00 ml, 1.4 M in cyclohexane, 28.00 mmol) was added to a solution of 2,3-dihydro-benzofuran (2.40 mL, 21.30 mmol) and tetramethylethylenediamine (TMEDA, 10.00 mL) in THF at −20° C. The resulting mixture was stirred for 1 hour, then DMF (3.00 mL, 38.75 mmol) was added and stirring was continued for another 30 minutes. The reaction mixture was quenched with water and diluted with ether. The resulting solution was washed with brine, dried over MgSO4 and concentrated to afford the desired title aldehyde.

Workup

  1. stirringstirring
  2. waitwas continued for another 30 minutes
  3. customThe reaction mixture was quenched with water
  4. additiondiluted with ether
  5. washThe resulting solution was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a58451d09f5a4acd8f266d937d0b7fb8
Source dataset
uspto-grants-2013_10
Patent number
US08557853B2

Reaction notes

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