Nitrogen → Benzaldehyde, 3-(2-methyl-1,3-dioxolan-2-yl)-

HRID 2064979Notes

Reaction equation

HRID 2064979 reaction equation
N#N.Br[C:4]1[CH:5]=[C:6]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[CH:7]=[CH:8][CH:9]=1.[Li]CCCC.CN([CH:24]=[O:25])C.[NH4+].[Cl-]>C1COCC1.CCCCCC>[CH3:15][C:10]1([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[CH:24]=[O:25])[O:14][CH2:13][CH2:12][O:11]1

Participants

8

Reactant 5

HCID 947NitrogenHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 109992182-(3-Bromophenyl)-2-methyl-1,3-dioxolaneHCID 178418339Butyllithium

Product 1

HCID 10607757Benzaldehyde, 3-(2-methyl-1,3-dioxolan-2-yl)-

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 2-(3-bromo-phenyl)-2-methyl-[1,3]dioxolane (944 mg, 3.88 mmol) in THF (20.0 mL) at −78° C. was added dropwise n-BuLi (1.60 mL of a 2.5M solution in hexane, 4.00 mmol). The reaction mixture was then stirred at −78° C. for 30 min before DMF (0.40 mL, 5.17 mmol) was added dropwise. The reaction mixture was allowed to warm to rt over 1 h. Sat. aq. NH4Cl was added and the mixture was extracted three times with Et2O. The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give the crude title compound as a pale yellow oil. LC-MS-conditions 02: tR=0.87 min.

Workup

  1. additionwas added dropwise
  2. extractionthe mixture was extracted three times with Et2O
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2f7f25f648ab4c1f971909437d1cc268
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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