Dimethylformamide → 6-Cyclopropylpicolinaldehyde

HRID 706550Notes

Reaction equation

HRID 706550 reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]2[CH2:15][CH2:14]2)[N:8]=1.CN([CH:19]=[O:20])C>C1COCC1>[CH:13]1([C:9]2[N:8]=[C:7]([CH:19]=[O:20])[CH:12]=[CH:11][CH:10]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 457878622-Bromo-6-cyclopropylpyridineHCID 178418339Butyllithium

Product 1

HCID 193617216-Cyclopropylpicolinaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A flame dried flask was charged with dry THF (75 mL) and chilled to −78° C. To this was added n-BuLi (9.90 mL, 24.7 mmol, 2.5 M in hexanes), followed by the slow addition of a THF (25 mL) solution of the 2-bromo-6-cyclopropylpyridine (4.90 g, 24.7 mmol) over a 15 minute period). The mixture was stirred at −78° C. for 15 minutes, and neat DMF (2.87 mL, 37.1 mmol) was added. The mixture was stirred for 15 minutes at −78° C., then quenched with saturated ammonium chloride solution (50 mL) and allowed to warm to ambient temperature. The mixture was diluted with water, extracted with EtOAc, dried over sodium sulfate and concentrated to 3.5 g (96%) of an orange oil/liquid.

Workup

  1. customA flame dried flask
  2. additionwas charged with dry THF (75 mL)
  3. stirringThe mixture was stirred for 15 minutes at −78° C.
  4. customquenched with saturated ammonium chloride solution (50 mL)
  5. temperatureto warm to ambient temperature
  6. additionThe mixture was diluted with water
  7. extractionextracted with EtOAc
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated to 3.5 g (96%) of an orange oil/liquid

Sources & evidence

ORD record
ord-bdb1c4cd9ae5446a89c8c6f64a0821ca
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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