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

HRID 1044781Notes

Reaction equation

HRID 1044781 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 (2.37 g, 9.74 mmol) in THF (20.0 mL) at −78° C. was added dropwise n-BuLi (4 mL of a 2.5M solution in hexane, 10.00 mmol). The reaction mixture was then stirred for 30 min at −78° C. before DMF (1.0 mL, 12.92 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 NaSO4, 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 NaSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b988ef73bd3f4f5aaebac00cdc5ed795
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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