Diethyl Ether → HCID 18675871, compound

HRID 1635091Notes

Reaction equation

HRID 1635091 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([CH2:11][CH3:12])[C:9]#N)[C:3]=1[O:13][CH3:14].CC(C[AlH]CC(C)C)C.C([O:26]CC)C>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([CH2:11][CH3:12])[CH:9]=[O:26])[C:3]=1[O:13][CH3:14]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 14487Diisobutylaluminum hydrideHCID 18675866HCID 18675866, compound

Product 1

HCID 18675871HCID 18675871, compound

Conditions

Temperature
-74 °C

Procedure

2-(4-Chloro-3-methoxy-2-pyridinyl)-butyronitrile (2.78 g) is dissolved in diethyl ether (150 ml), the solution is cooled to −74° C. and DIBAL (29 ml 1.0M) is added over a 30 min period. The solution is allowed to stir at −74° C. for an hour then at 0° C. for another hour. The reaction is quenched by addition of 5% sulfuric acid (25 ml), keeping the temperature around 0° C. The phases are separated and the organic phase washed with a solution of sodium bicarbonate, dried and evaporated to afford the desired product.

Workup

  1. waitat 0° C. for another hour
  2. customThe reaction is quenched by addition of 5% sulfuric acid (25 ml)
  3. customthe temperature around 0° C
  4. customThe phases are separated
  5. washthe organic phase washed with a solution of sodium bicarbonate
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-d41eb6be4fa54e26a4f74842e7fcf8b8
Source dataset
uspto-grants-2003_01
Patent number
US06509349B1

Reaction notes

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