Dimethylformamide → 4-(1-Methylpyrrolidin-2-yl)benzaldehyde

HRID 908027Notes

Reaction equation

HRID 908027 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[CH3:13])=[CH:4][CH:3]=1.[Li]CCCC.CN([CH:22]=[O:23])C>C1COCC1>[CH3:13][N:9]1[CH2:10][CH2:11][CH2:12][CH:8]1[C:5]1[CH:6]=[CH:7][C:2]([CH:22]=[O:23])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2848972-(4-Bromophenyl)-1-methylpyrrolidineHCID 178418339Butyllithium

Product 1

HCID 866390414-(1-Methylpyrrolidin-2-yl)benzaldehydeYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-bromophenyl)-1-methylpyrrolidine (0.45 g, 2 mmol) in dry THF (10 mL) was added dropwise n-BuLi (0.88 mL, 2.2 mmol, 2.5 mol/L in hexane) at −78° C., after the addition was completed the mixture was stirred for 1 h, then dry DMF (0.18 mL, 2.4 mmol) was added to the reaction system and stirring was continued for another 1 hr. Then the reaction mixture was partitioned between EtOAc and 1 N HCl, the aqueous solution was extracted with EtOAc (3×15 mL). The combined organic phase was washed with brine, dried over Na2SO4, and concentrated in vacuo to give crude product (0.28 g, yield 74%) as a yellow oil. The product was used directly in the next step without further purification. LC-MS (ESI) m/z: 189 (M+1)+.

Workup

  1. additionafter the addition
  2. stirringstirring
  3. waitwas continued for another 1 hr
  4. customThen the reaction mixture was partitioned between EtOAc and 1 N HCl
  5. extractionthe aqueous solution was extracted with EtOAc (3×15 mL)
  6. washThe combined organic phase was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57a906eba1284350881daaa2e631882e
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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