Dimethylformamide → Benzaldehyde, 2-(3-butenyl)-

HRID 921202Notes

Reaction equation

HRID 921202 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH:10]=[CH2:11].[Li]CCCC.CN(C)[CH:19]=[O:20]>C1COCC1>[CH2:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:19]=[O:20])[CH2:9][CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 34857122-(But-3-en-1-yl)bromobenzeneHCID 178418339Butyllithium

Product 1

HCID 10261375Benzaldehyde, 2-(3-butenyl)-Yield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-bromo-2-(but-3-en-1-yl)benzene (1 g, 4.74 mmol) in THF (15 mL) at −78° C. was added BuLi (2.274 mL, 5.68 mmol) dropwise. It was stirred at this temperature for 1 h, then N,N-dimethylformamide (0.416 g, 5.68 mmol) was added and stirred at −78° C. for 30 min. then warmed up to rt and stirred at rt for 1 h. It was then quenched with NH4Cl, extracted with ether. The organic layer was then dried over MgSO4, filtered and concentrated to obtain 2-(but-3-en-1-yl)benzaldehyde (0.7 g, 92%) as an oil. 1H NMR (400 MHz, CDCl3) δ 10.35-10.26 (m, 1H), 7.86 (dd, J=7.6, 1.5 Hz, 1H), 7.54 (td, J=7.5, 1.6 Hz, 1H), 7.44-7.38 (m, 1H), 7.30 (d, J=8.1 Hz, 1H), 5.95-5.83 (m, 1H), 5.09-5.00 (m, 2H),), 3.20-3.12 (m, 2H), 2.44-2.36 (m, 2H).

Workup

  1. stirringstirred at −78° C. for 30 min.
  2. stirringstirred at rt for 1 h
  3. customIt was then quenched with NH4Cl
  4. extractionextracted with ether
  5. dry with materialThe organic layer was then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-410066ab0d1240de8e54298dc4f0138c
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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