Dimethylformamide → 8-Chloro-4,4-dimethylchroman-6-carbaldehyde

HRID 402787Notes

Reaction equation

HRID 402787 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2([CH3:14])[CH3:13].[Li]CCCC.CN([CH:23]=[O:24])C>C1COCC1>[Cl:12][C:10]1[CH:11]=[C:2]([CH:23]=[O:24])[CH:3]=[C:4]2[C:9]=1[O:8][CH2:7][CH2:6][C:5]2([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 667651386-Bromo-8-chloro-4,4-dimethylchromanHCID 178418339Butyllithium

Product 1

HCID 772308588-Chloro-4,4-dimethylchroman-6-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

6-Bromo-8-chloro-4,4-dimethyl-3,4-dihydro-2H-chromene (483 mg, 1.75 mmol) in THF (12.0 mL) under N2 atmosphere was cooled to −78° C., and n-BuLi (841 μL, 2.10 mmol) was added dropwise via a syringe. The reaction mixture was stirred at −78° C. for 10 minutes and then DMF (543 μL, 7.01 mmol) was added dropwise via a syringe. The resulting mixture was allowed to warm to room temperature and wet silica gel (5.0 g/0.5 mL of water) was added. The mixture was allowed to stir at room temperature for 10 minutes before it was filtered. The silica gel was rinsed with EtOAc, and the filtrate was concentrated under vacuum. The crude residue was purified by silica gel chromatography eluting with 0-20% EtOAc/hexanes to obtain the title compound as a white solid.

Workup

  1. temperatureto warm to room temperature
  2. additionwet silica gel (5.0 g/0.5 mL of water) was added
  3. stirringto stir at room temperature for 10 minutes before it
  4. filtrationwas filtered
  5. washThe silica gel was rinsed with EtOAc
  6. concentrationthe filtrate was concentrated under vacuum
  7. customThe crude residue was purified by silica gel chromatography
  8. washeluting with 0-20% EtOAc/hexanes

Sources & evidence

ORD record
ord-1a58b73a706549c08733fc9e47496166
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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