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

HRID 1363666Notes

Reaction equation

HRID 1363666 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(CCN(C)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 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 aldehydei. i Tasker, Andrew S.; Sorensen, Bryan K.; Jae, Hwan-Soo; Winn, Martin; Geldern, Thomas W. von; et al. J. Med. Chem. 1997, 40, 322-330.

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
  8. customto afford the desired title aldehydei

Sources & evidence

ORD record
ord-e629fe8dfaab44fdace49b8c90e18ed3
Source dataset
uspto-grants-2011_02
Patent number
US07884244B2

Reaction notes

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